Condensed heterocyclic derivatives and herbicides

ABSTRACT

A condensed heterocyclic derivative of the formula ##STR1## (wherein R is a hydroxyl group, R 3  or R 4  is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.

This is a Division of application Ser. No. 08/204,199 filed on Mar. 1, 1994, now U.S. Pat. No. 5,616,537, which was filed as International Application PCT/JP93/00909 on Jul. 2, 1993.

TECHNICAL FIELD

The present invention relates to condensed heterocyclic derivatives and their salts as well as herbicides containing them as active ingredients, which can be applied to paddy fields, upland fields and non-agricultural fields.

BACKGROUND ART

The present inventors found that quinoline and naphthalene derivatives have herbicidal activities and disclosed specific examples in Japanese Unexamined Patent Publication No. 56469/1990. Further, Japanese Unexamined Patent Publication No. 121973/1990 discloses that aromatic carboxylic acid derivatives containing quinoline, naphthalene, benzofuran, thiophene or pyridine ring have herbicidal activities.

However, the above-mentioned publications disclose nothing about specific compounds relating to the condensed heterocyclic derivatives of the present invention. Further, these compounds are not necessarily satisfactory from the viewpoint of the herbicidal effects. A number of other herbicides have been developed and contributed to the saving of energy for agricultural operations and to the improvement of the productivity. However, in their practical use, such herbicides also have various problems with respect to the herbicidal effects and the safety to crop plants.

The present inventors have conducted an extensive research on condensed heterocyclic derivatives with an object to develop a compound which is excellent in the herbicidal activities without bringing about phytotoxicity to crop plants. As a result, it has been found that the compounds of the present invention which are pyrimidine or triazine derivatives bonded to a condensed heterocyclic ring exhibit excellent herbicidal activities against not only annual weeds but also perennial gramineous weeds, cyperaceous weeds and broad leaf weeds in the paddy field treatment, upland soil treatment and foliage treatment, and they are highly safe to crop plants. The present invention has been accomplished on the basis of this discovery.

DISCLOSURE OF THE INVENTION

Namely, the present invention relates to a condensed heterocyclic derivative of the formula (I): ##STR2## {wherein A is a heterocyclic ring of the formula ##STR3## R is a hydrogen atom, a hydroxyl group, an alkoxy group which may be substituted, a benzyloxy group which may be substituted, an aryloxy group which may be substituted, an alkylthio group which may be substituted, a benzylthio group which may be substituted, an arylthio group which may be substituted, an alkenyloxy group which may be substituted, an alkynyloxy group which may be substituted, an alkenylthio group which may be substituted, an alkynylthio group which may be substituted, an alkylideneaminoxy group, or a group of the formula --NR⁶ R⁷ (wherein each of R⁶ and R⁷ which may be the same or different, is a hydrogen atom, an alkyl group, an alkoxy group, a benzyl group, an aryl group which may be substituted, an alkylsulfonyl group, or an arylsulfonyl group which may be substituted, or R⁶ and R⁷ may, together with the nitrogen atom, form a ring which may contain a hetero atom), each of R¹ and R² which may be the same or different, is a hydrogen atom, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, a carboxyl group, a group of the formula --CONR⁶ R⁷ (wherein R⁶ and R⁷ are as defined above), an alkylthiocarbonyl group which may be substituted, a cycloalkylthiocarbonyl group, an aryloxycarbonyl group which may be substituted, an alkoxycarbonyl group which may be substituted, a cycloalkyl group, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an aryl group which may be substituted, a halogen atom, a benzyloxycarbonyl group which may be substituted, a benzylthiocarbonyl group which may be substituted, a cycloalkoxycarbonyl group, an arylthiocarbonyl group which may be substituted, an alkenyloxycarbonyl group which may be substituted, an alkynyloxycarbonyl group which may be substituted, an alkenylthiocarbonyl group which may be substituted, an alkynylthiocarbonyl group which may be substituted, an isopropylideneaminoxycarbonyl group, a nitro group, a cyano group, a halogenated carbonyl group, a group of the formula CR⁸ ═N--R⁹ (wherein R⁸ is a hydrogen atom, an aryl group, or an alkyl group, and R⁹ is a hydroxyl group, an alkyl group, an aryl group which may be substituted, a benzyl group which may be substituted, a benzyloxy group which may be substituted, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a phenoxy group which may be substituted, an alkylamino group, a dialkylamino group, an arylamino group which may be substituted, or an arylsulfonylamino group which may be substituted), a group of the formula NR¹⁰ R¹¹ (wherein each of R¹⁰ and R¹¹ which may be the same or different, is a hydrogen atom, an alkyl group, an aryl group which may be substituted, a benzyl group which may be substituted, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, an alkoxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group which may be substituted, a carbamoyl group, an alkylthiocarbonyl group or an arylthiocarbonyl group which may be substituted, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a ring which may contain a hetero atom), a group of the formula N═CR¹² R¹³ (wherein each of R¹² and R¹³ which may be the same or different, is a hydrogen atom, an alkyl group, or an aryl group which may be substituted, or R¹² and R¹³ may form a ring which may contain a hetero atom), each of R³ and R⁴ which may be the same or different, is a hydrogen atom, an alkoxy group which may be substituted, a halogen atom, an alkylamino group, a dialkylamino group, or an alkyl group which may be substituted, R⁵ is a hydrogen atom, an alkyl group which may be substituted, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a benzyloxycarbonyl group, an alkylthiocarbonyl group, an arylthiocarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a trialkylsilyl group, an alkenyl group, an alkynyl group, a 4,6-dimethoxypyridin-2-yl group, or trichloromethylthio group, each of X¹ and X² which may be the same or different, is an oxygen atom, a sulfur atom, a methylene group, a group of the formula NR¹⁴ (wherein R¹⁴ is a hydrogen atom or an alkyl group), a carbonyl group, a group of the formula C═NOR¹⁵ (wherein R¹⁵ is an alkyl group), or a hydroxymethylene group, Q¹ is a methylene group, a carbonyl group, or a group of the formula C═C<R¹⁶ R¹⁷ (wherein each of R¹⁶ and R¹⁷ which may be the same or different, is a cyano group, a cycloalkylcarbonyl group, a benzoyl group, or an alkoxycarbonyl group), each of Q² and Q³ which may be the same or different is a group of the formula C<R¹⁸ R¹⁹ wherein each of R¹⁸ and R¹⁹ which may be the same or different, is a hydrogen atom, an alkyl group, or an alkoxycarbonyl group, or R¹⁸ and R¹⁹ together form a carbonyl group or a group of the formula C═CHR²⁰ (wherein R²⁰ is a hydrogen atom or an alkyl group)!, and each of a, b, d and e is a nitrogen atom or a methine group, provided that at least one of them is a nitrogen atom (provided that a case where each of a, b and d is a methine group and e is a nitrogen atom, and the formula (I) represents a 8-quinolinecarboxylic acid derivative, is excluded), Y is a halogen atom, an alkyl group which may be substituted, an alkoxy group, a phenyl group which may be substituted, a nitro group, an alkylamino group, or a dialkylamiono group, n is an integer of from 0 to 2, provided that when n is 2, it may represents a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group or a nitrogen atom}, or its salt; and a herbicide containing it as an active ingredient.

As preferred compounds, among them, those of the formula (I) wherein R is a hydrogen atom, a hydroxyl group and a C₁ -C₆ alkoxy group, may, for example, be mentioned. R³ and R⁴ may, for example, be a halogen atom, which may be a chlorine, bromine, fluorine or iodine atom, a C₁ -C₆ alkyl group or an alkoxy group.

Further, R¹ and R² may, for example, be a C₁ -C₈ alkyl group, a formyl group, a C₁ -C₈ alkylcarbonyl group, a C₁ -C₈ alkoxycarbonyl group, a C₁ -C₈ alkylthiocarbonyl group, a C₁ -C₈ cycloalkoxycarbonyl group, a C₁ -C₈ cycloalkylthiocarbonyl group, a C₃ -C₆ alkenyloxycarbonyl group which may be substituted, a C₃ -C₆ alkenylthiocarbonyl group, a C₃ -C₆ alkynyloxycarbonyl group which may be substituted, or a C₃ -C₆ alkynylthiocarbonyl group, and R⁵ may, for example, be a hydrogen atom, a formyl group, or a C₁ -C₈ alkylcarbonyl group. Now, specific examples of the compound of the present invention will be shown in Tables 1 to 59. The compound numbers will be referred to in the subsequent description.

                                      TABLE 1                                      __________________________________________________________________________      ##STR4##                                                                      Compound                         m.p. (°C.)                             No.   R.sup.1                                                                           R.sup.2                                                                              R         W X Yn                                                                               Z or (n.sub.D.sup.20)                           __________________________________________________________________________     1     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR5## O O H CH                                                                               127-131                                       2     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OH        O O H CH                                                                               160-163                                       3     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OCH.sub.3 O O H CH                                                                               132-133.5                                     4     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR6## O O H CH                                                                               92-93                                         5     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   NHSO.sub.2 CH.sub.3                                                                      O O H CH                                              6     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OCH.sub.2 COOC.sub.2 H.sub.5                                                             O O H CH                                                                               92-94.5                                       7     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OC.sub.2 H.sub.5                                                                         O O H CH                                                                               130-131                                       8     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR7## O O H CH                                                                               106.5-109                                     9     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR8## O O H CH                                                                               153-157                                       10    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR9## O O H CH                                                                               130.5-132                                     11    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR10##                                                                               O O H CH                                                                               112.5-114                                     12    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                                                               113-116                                       13    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR11##                                                                               O O H CH                                                                               1.5429                                        14    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OC.sub.3 H.sub.7                                                                         O O H CH                                                                               119-121                                       15    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OC.sub.3 H.sub.7 -i                                                                      O O H CH                                                                               88.5-90                                       __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________     Compound                           m.p. (°C.)                           No.   R.sup.1                                                                           R.sup.2 R         W X Yn                                                                               Z or (n.sub.D.sup.20)                         __________________________________________________________________________     16    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                      ##STR12##                                                                               O O H CH                                                                               146-148                                     17    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                      ##STR13##                                                                               S O H CH                                            18    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                     OH        S O H CH                                            19    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                      ##STR14##                                                                               S O H CH                                            20    CH.sub.3                                                                          COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i                                                   ##STR15##                                                                               O O H CH                                                                               141-144                                     21    CH.sub.3                                                                          COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i                                                  OH        O O H CH                                                                               140.5-143                                   22    CH.sub.3                                                                          COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i                                                   ##STR16##                                                                               O O H CH                                                                               1.5310                                      23    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR17##                                                                               O O H CH                                                                               1.5839                                      24    CH.sub.3                                                                          COOCH.sub.3                                                                            OH        O O H CH                                                                               174-178                                     25    CH.sub.3                                                                          COOCH.sub.3                                                                            OCH.sub.3 O O H CH                                            26    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR18##                                                                               O O H CH                                                                               126-130                                     27    CH.sub.3                                                                          COOCH.sub.3                                                                            OH        S O H CH                                                                               219-223 6549                                28    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR19##                                                                               S O H CH                                            29    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR20##                                                                               S O H CH                                            30    CH.sub.3                                                                          COOCH.sub.3                                                                            OH        O O H N 182-185                                     __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________     Compound                           m.p. (°C.)                           No.   R.sup.1                                                                           R.sup.2 R         W X Yn                                                                               Z or (n.sub.D.sup.20)                         __________________________________________________________________________     31    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR21##                                                                               O O H N 88-90                                       32    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR22##                                                                               O O H N 120-122                                     33    CH.sub.3                                                                          COOCH.sub.3                                                                            OH        S O H N                                             34    CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                     OH        O O H CH                                                                               162-166                                     35    CH.sub.3                                                                          COOC.sub.4 H.sub.9 -s                                                                  OH        O O H CH                                                                               144-147.5                                   36    CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                     OH        O O H CH                                                                               160-164                                     37    CH.sub.3                                                                          CONH.sub.2                                                                             OH        O O H CH                                            38    CH.sub.3                                                                          COOH    OH        O O H CH                                                                               186-188                                     39    CH.sub.3                                                                          COCH.sub.3                                                                              ##STR23##                                                                               O O H CH                                                                               62-65                                       40    CH.sub.3                                                                          COCH.sub.3                                                                             OH        O O H CH                                                                               166-169                                     41    CH.sub.3                                                                          COCH.sub.3                                                                             OCH.sub.3 O O H CH                                                                               178-181                                     42    CH.sub.3                                                                          COCH.sub.3                                                                              ##STR24##                                                                               O O H CH                                                                               122-125                                     43    CH.sub.3                                                                          COCH.sub.3                                                                             NHSO.sub.2 CH.sub.3                                                                      O O H CH                                            44    CH.sub.3                                                                           ##STR25##                                                                             OCH.sub.3 O O H CH                                                                               101-103                                     45    CH.sub.3                                                                           ##STR26##                                                                              ##STR27##                                                                               O O H CH                                                                               1.5778                                      46    CH.sub.3                                                                           ##STR28##                                                                             OH        O O H CH                                            47    CH.sub.3                                                                           ##STR29##                                                                              ##STR30##                                                                               O O H CH                                                                               120-123                                     48    CH.sub.3                                                                           ##STR31##                                                                             OH        O O H CH                                                                               184-187                                     __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2      R       W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     49    CH.sub.3                                                                           ##STR32##   OCH.sub.3                                                                              O O H CH                                                                               169-172                                  50    CH.sub.3                                                                           ##STR33##                                                                                   ##STR34##                                                                             O O H CH                                                                               115-117                                  51    CH.sub.3                                                                           ##STR35##   OCH.sub.3                                                                              O O H CH                                                                               133-137                                  52    CH.sub.3                                                                           ##STR36##   OCH.sub.2 OC.sub.2 H.sub.5                                                             O O H CH                                                                               127-130                                  53    CH.sub.3                                                                           ##STR37##   OCH.sub.3                                                                              O O H CH                                                                               168-170.5                                54    CH.sub.3                                                                           ##STR38##   OH      O O H CH                                         55    CH.sub.3                                                                           ##STR39##   OCH.sub.3                                                                              O O H CH                                                                               128-131                                  56    CH.sub.3                                                                           ##STR40##   OH      O O H CH                                         57    CH.sub.3                                                                           ##STR41##   OCH.sub.3                                                                              O O H CH                                                                               170-173.5                                58    CH.sub.3                                                                           ##STR42##   OH      O O H CH                                         59    CH.sub.3                                                                          COC.sub.4 H.sub.9 -i                                                                        OH      O O H CH                                                                               168-171                                  60    CH.sub.3                                                                          CN           OH      O O H CH                                                                               175-179                                  __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________     Compound                           m.p. (°C.)                           No.   R.sup.1                                                                           R.sup.2 R         W X Yn                                                                               Z or (n.sub.D.sup.20)                         __________________________________________________________________________     61    H  COOC.sub.2 H.sub.5                                                                     OH        O O H CH                                                                               161-163                                     62    H  COOC.sub.2 H.sub.5                                                                      ##STR43##                                                                               O O H CH                                                                               1.5351                                      63    H  COOC.sub.2 H.sub.5                                                                      ##STR44##                                                                               O O H CH                                                                               91.5-93                                     64    H  CN      OH        O O H CH                                            65    H  CN                                                                                      ##STR45##                                                                               O O H CH                                            66    H  CN                                                                                      ##STR46##                                                                               O O H CH                                            67    CF.sub.3                                                                          COOCH.sub.3                                                                            OH        O O H CH                                            68    CH.sub.3                                                                          COC.sub.4 H.sub.9 -i                                                                    ##STR47##                                                                               O O H CH                                                                               1.5765                                      69    CF.sub.3                                                                           ##STR48##                                                                             OCH.sub.3 O O H CH                                                                               155-158                                     70    CF.sub.3                                                                           ##STR49##                                                                             OH        O O H CH                                                                               178-181                                     71    C.sub.2 H.sub.5                                                                   COOC.sub.2 H.sub.5                                                                     OH        O O H CH                                                                               159.5-162                                   72    C.sub.2 H.sub.5                                                                   COOC.sub.2 H.sub.5                                                                      ##STR50##                                                                               O O H CH                                                                               116-120                                     73    C.sub.2 H.sub.5                                                                   COOC.sub.2 H.sub.5                                                                      ##STR51##                                                                               O O H CH                                                                               1.5339                                      74    C.sub.2 H.sub.5                                                                   COOC.sub.3 H.sub.7                                                                     OH        O O H CH                                                                               119-122                                     __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                              R.sup.2 R         W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     75    C.sub.2 H.sub.5                                                                      COOC.sub.3 H.sub.7                                                                      ##STR52##                                                                               O O H CH                                                                               108-109.5                                76    C.sub.2 H.sub.5                                                                      COOC.sub.3 H.sub.7 -i                                                                  OH        O O H CH                                                                               137-140                                  77    CF.sub.3                                                                              ##STR53##                                                                             O.sup.-  Na.sup.+                                                                        O O H CH                                                                               >300                                     78    CF.sub.3                                                                              ##STR54##                                                                              ##STR55##                                                                               O O H CH                                                                               143-146                                  79    CH.sub.2 Cl                                                                          COOC.sub.2 H.sub.5                                                                     OH        O O H CH                                         80    C.sub.2 H.sub.5                                                                      COOC.sub.3 H.sub.7 -i                                                                   ##STR56##                                                                               O O H CH                                                                               94-96                                    81    CH.sub.2 Cl                                                                          COOC.sub.2 H.sub.5                                                                      ##STR57##                                                                               O O H CH                                         82                                                                                    ##STR58##                                                                           COCH.sub.3                                                                             OCH.sub.3 O O H CH                                                                               151-154.5                                83                                                                                    ##STR59##                                                                           COCH.sub.3                                                                             OH        O O H CH                                         84                                                                                    ##STR60##                                                                            ##STR61##                                                                              ##STR62##                                                                               O O H CH                                                                               176.5-180                                85                                                                                    ##STR63##                                                                            ##STR64##                                                                             OH        O O H CH                                                                               178.5-181                                86                                                                                    ##STR65##                                                                            ##STR66##                                                                              ##STR67##                                                                               O O H CH                                                                               Unmeasurable                             __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                               R.sup.2                                                                             R         W X Yn                                                                               Z or (n.sub.D.sup.20)                        __________________________________________________________________________     87                                                                                    ##STR68##                                                                            COOC.sub.2 H.sub.5                                                                   ##STR69##                                                                               O O H CH                                                                               85-90                                      88                                                                                    ##STR70##                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O H CH                                                                               154-158                                    89                                                                                    ##STR71##                                                                            COOC.sub.2 H.sub.5                                                                   ##STR72##                                                                               O O H CH                                                                               1.5730                                     90                                                                                    ##STR73##                                                                            CN                                                                                   ##STR74##                                                                               O O H CH                                                                               152-156                                    91                                                                                    ##STR75##                                                                            CN   OH        O O H CH                                                                               165-169                                    92                                                                                    ##STR76##                                                                            CN   OCH.sub.3 O O H CH                                           93                                                                                    ##STR77##                                                                            CN                                                                                   ##STR78##                                                                               O O H CH                                                                               143-146                                    94                                                                                    ##STR79##                                                                             ##STR80##                                                                          OCH.sub.3 O O H CH                                                                               138-140                                    95                                                                                    ##STR81##                                                                             ##STR82##                                                                          OH        O O H CH                                           96                                                                                    ##STR83##                                                                            COCH.sub.3                                                                          OCH.sub.3 O O H CH                                                                               137-141                                    97                                                                                    ##STR84##                                                                            COCH.sub.3                                                                          OH        O O H CH                                           __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.1                                                                             R.sup.2                                                                             R         W X Yn   Z or (n.sub.D.sup.20)                       __________________________________________________________________________      98   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O 7-Cl CH                                           99   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O 7-CH.sub.3                                                                          CH                                          100   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O 6-Cl CH                                          101   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O 6-CH.sub.3                                                                          CH                                          102   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O 7-OCH.sub.3                                                                         CH                                          103   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O 6-N(CH.sub.3).sub.2                                                                 CH                                          104   H    CH.sub.3                                                                            H         O S H    CH                                                                               158-161                                   105   H    CH.sub.3                                                                            OH        O S H    CH                                                                               172-175                                   106   H    CH.sub.3                                                                             ##STR85##                                                                               O S H    CH                                          107   H    CH.sub.3                                                                            OCH.sub.3 O S H    CH                                          108   COOCH.sub.3                                                                         CH.sub.3                                                                            H         O S H    CH                                                                               201-206                                   109   COOCH.sub.3                                                                         CH.sub.3                                                                            OH        O S H    CH                                                                               154-158.5                                 110   COOCH.sub.3                                                                         CH.sub.3                                                                             ##STR86##                                                                               O S H    CH                                          111   COOCH.sub.3                                                                         CH.sub.3                                                                             ##STR87##                                                                               O S H    CH                                          112   CH.sub.3                                                                            COOCH.sub.3                                                                         OH        O S H    CH                                                                               153-155                                   113   CH.sub.3                                                                            COOCH.sub.3                                                                          ##STR88##                                                                               O S H    CH                                          114   CH.sub.3                                                                            COOCH.sub.3                                                                         OCH.sub.3 O S H    CH                                          115   CH.sub.3                                                                            COOCH.sub.3                                                                          ##STR89##                                                                               O S H    CH                                          116   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O S H    CH                                                                               155-158                                   117   H    H    OH        O S H    CH                                          118   H    H                                                                                    ##STR90##                                                                               O S H    CH                                          __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                             R.sup.2                                                                             R         W X   Yn                                                                               Z or (n.sub.D.sup.20)                        __________________________________________________________________________     119   H    H                                                                                    ##STR91##                                                                               O S   H CH                                           120   H    H    OCH.sub.3 O S   H CH                                           121   H    H    OH        O S   H N                                            122   H    CH.sub.3                                                                            OH        O S   H N                                            123   H    CH.sub.3                                                                            OH        S S   H CH                                           124   H    CH.sub.3                                                                            OH        O NCH.sub.3                                                                          H CH                                           125   H    CH.sub.3                                                                            OH        O NCH.sub.3                                                                          H N                                            126   H    CH.sub.3                                                                            OH        S NCH.sub.3                                                                          H CH                                           127   COOCH.sub.3                                                                         CH.sub.3                                                                            OH        O NCH.sub.3                                                                          H CH                                           128   CH.sub.3                                                                            COOCH.sub.3                                                                          ##STR92##                                                                               O O   H CH                                           129   CH.sub.3                                                                            COOCH.sub.3                                                                          ##STR93##                                                                               O O   H N                                            130   CH.sub.3                                                                            COOCH.sub.3                                                                         O.sup.-  Na.sup.+                                                                        O O   H CH                                                                               >300                                       131   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                   ##STR94##                                                                               O NH  H CH                                                                               196-199                                    132   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O NH  H CH                                                                               202-204                                    133   H    COCH.sub.3                                                                          OH        O O   H CH                                           __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.1                                                                            R.sup.2  R         W    X Yn                                                                               Z or (n.sub.D.sup.20)                    __________________________________________________________________________     134   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                      SCH.sub.3 O    O H CH                                       135   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                      SC.sub.2 H.sub.5                                                                         O    O H CH                                       136   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                       ##STR95##                                                                               O    O H CH                                       137   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                      OH        N(CHO)                                                                              O H CH                                       138   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                      OH        CH.sub.2                                                                            O H CH                                       139   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                      OH        CH(CN)                                                                              O H CH                                       140   CH.sub.3                                                                           COOCH.sub.3                                                                             NH.sub.2  O    O H CH                                       141   CH.sub.3                                                                           COOCH.sub.3                                                                             NHCH.sub.3                                                                               O    O H CH                                       142   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                      N(CH.sub.3).sub.2                                                                        O    O H CH                                       143   COCH.sub.3                                                                         CH.sub.3                                                                                 ##STR96##                                                                               O    O H CH                                       144   COCH.sub.3                                                                         CH.sub.3 OH        O    O H CH                                       145   COCH.sub.3                                                                         CH.sub.3                                                                                 ##STR97##                                                                               O    O H CH                                       146   CH.sub.3                                                                            ##STR98##                                                                               ##STR99##                                                                               O    O H CH                                       147   CH.sub.3                                                                            ##STR100##                                                                             OH        O    O H CH                                                                               143-146                                148   CH.sub.3                                                                            ##STR101##                                                                              ##STR102##                                                                              O    O H CH                                       149   CH.sub.3                                                                           COSCH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                                                                     O    O H CH                                                                               134-136                                150   CH.sub.3                                                                           COSCH.sub.3                                                                             OH        O    O H CH                                                                               163-165                                151   CH.sub.3                                                                           COSCH.sub.3                                                                              ##STR103##                                                                              O    O H CH                                       152   CH.sub.3                                                                           COSC.sub.2 H.sub.5                                                                      OCH.sub.2 CHCH.sub.2                                                                     O    O H CH                                                                               102-105                                153   CH.sub.3                                                                           COSC.sub.2 H.sub.5                                                                      OH        O    O H CH                                                                               149-152                                __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                           R.sup.2                                                                              R         W X Yn                                                                               Z or (n.sub.D.sup.20)                           __________________________________________________________________________     154   CH.sub.3                                                                          COSC.sub.2 H.sub.5                                                                    ##STR104##                                                                              O O H CH                                              155   CH.sub.3                                                                          CONHCH.sub.3                                                                         OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                              156   CH.sub.3                                                                          CONHCH.sub.3                                                                         OH        O O H CH                                              157   CH.sub.3                                                                          CONHCH.sub.3                                                                          ##STR105##                                                                              O O H CH                                              158   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                           OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               96-98                                         159   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                           OH        O O H CH                                                                               183-186                                       160   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                            ##STR106##                                                                              O O H CH                                              161   CH.sub.3                                                                           ##STR107##                                                                          OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               85-88                                         162   CH.sub.3                                                                           ##STR108##                                                                          OH        O O H CH                                                                               180-182.5                                     163   CH.sub.3                                                                           ##STR109##                                                                           ##STR110##                                                                              O O H CH                                              164   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                    ##STR111##                                                                              O O H CH                                                                               132-136                                       165   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                    ##STR112##                                                                              O O H CH                                                                               108-109                                       166   CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                    ##STR113##                                                                              O O H CH                                                                               135-136.5                                     167   CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                    ##STR114##                                                                              O O H CH                                                                               1.5209                                        __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                           R.sup.2                                                                              R         W X Yn                                                                               Z or (n.sub.D.sup.20)                           __________________________________________________________________________     168   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -s                                                                 ##STR115##                                                                              O O H CH                                                                               149-150.5                                     169   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -s                                                                 ##STR116##                                                                              O O H CH                                                                               90-91.5                                       170   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -i                                                                 ##STR117##                                                                              O O H CH                                                                               152-156                                       171   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -i                                                                OH        O O H CH                                                                               135-138                                       172   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -i                                                                 ##STR118##                                                                              O O H CH                                                                               1.5276                                        173   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                 ##STR119##                                                                              O O H CH                                                                               170-172                                       174   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                OH        O O H CH                                                                               153-157                                       175   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                 ##STR120##                                                                              O O H CH                                              176   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                              177   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                   ##STR121##                                                                              O O H CH                                                                               115-116.5                                     178   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                  OH        O O H CH                                                                               140-144                                       179   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                   ##STR122##                                                                              O O H CH                                                                               1.5291                                        180   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                  OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                              181   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                   ##STR123##                                                                              O O H CH                                                                               99-101                                        182   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                  OH        O O H CH                                                                               153-159                                       __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________     Compound                          m.p. (°C.)                            No.   R.sup.1                                                                           R.sup.2                                                                               R         W X Yn                                                                               Z or (n.sub.D.sup.20)                          __________________________________________________________________________     183   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                    ##STR124##                                                                              O O H CH                                                                               1.5280                                       184   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                   OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                             185   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                    ##STR125##                                                                              O O H CH                                                                               78-80                                        186   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                   OH        O O H CH                                                                               145-149                                      187   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                    ##STR126##                                                                              O O H CH                                                                               1.5288                                       188   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                   OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                             189   CH.sub.3                                                                          COOC.sub.8 H.sub.17                                                                    ##STR127##                                                                              O O H CH                                                                               105-108                                      190   CH.sub.3                                                                          COOC.sub.8 H.sub.17                                                                   OH        O O H CH                                                                               148-151                                      191   CH.sub.3                                                                          COOC.sub.8 H.sub.17                                                                    ##STR128##                                                                              O O H CH                                                                               1.5170                                       192   CH.sub.3                                                                           ##STR129##                                                                            ##STR130##                                                                              O O H CH                                                                               99-101                                       193   CH.sub.3                                                                           ##STR131##                                                                           OH        O O H CH                                                                               130-132                                      194   CH.sub.3                                                                           ##STR132##                                                                            ##STR133##                                                                              O O H CH                                                                               1.5260                                       195   CH.sub.3                                                                           ##STR134##                                                                           OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                             196   CH.sub.3                                                                           ##STR135##                                                                            ##STR136##                                                                              O O H CH                                             197   CH.sub.3                                                                           ##STR137##                                                                           OH        O O H CH                                                                               115-119                                      __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2 R          W X Yn                                                                               Z or (n.sub.D.sup.20)                        __________________________________________________________________________     198   CH.sub.3                                                                           ##STR138##                                                                             ##STR139##                                                                               O O H CH                                           199   CH.sub.3                                                                           ##STR140##                                                                            OCH.sub.2 OC.sub.2 H.sub.5                                                                O O H CH                                           200   CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                                                     ##STR141##                                                                               O O H CH                                                                               147-149                                    201   CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                                                    OH         O O H CH                                                                               200-203                                    202   CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                                                    OCH.sub.2 CCH.sub.2                                                                       O O H CH                                                                               Unmeasurable                               203   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR142##                                                                               O O H CH                                                                               140-143                                    204   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                  OH         O O H CH                                                                               167-170                                    205   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR143##                                                                               O O H CH                                                                               Unmeasurable                               206   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR144##                                                                               O O H CH                                           207   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                  OCH.sub.2 OC.sub.2 H.sub.5                                                                O O H CH                                           208   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                  O.sup.-  Na.sup.+                                                                         O O H CH                                                                               208-210                                    209   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR145##                                                                               O O H CH                                           210   CH.sub.3                                                                           ##STR146##                                                                             ##STR147##                                                                               O O H CH                                                                               183-184.5                                  211   CH.sub.3                                                                           ##STR148##                                                                            OH         O O H CH                                                                               161-164.5                                  __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2    R         W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     212   CH.sub.3                                                                           ##STR149##                                                                                ##STR150##                                                                              O O H CH                                         213   CH.sub.3                                                                           ##STR151##                                                                                ##STR152##                                                                              O O H CH                                                                               194-196                                  214   CH.sub.3                                                                           ##STR153##                                                                               OH        O O H CH                                                                               103-105                                  215   CH.sub.3                                                                           ##STR154##                                                                                ##STR155##                                                                              O O H CH                                                                               1.5334                                   216   CH.sub.3                                                                           ##STR156##                                                                               OH        O O H CH                                                                               142-144                                  217   CH.sub.3                                                                           ##STR157##                                                                                ##STR158##                                                                              O O H CH                                         218   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                     ##STR159##                                                                              O O H CH                                                                               101.5-104                                219   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                    OH        O O H CH                                                                               163-165                                  220   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                     ##STR160##                                                                              O O H CH                                         221   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                     ##STR161##                                                                              O O H CH                                                                               1.5322                                   222   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                            ##STR162##                                                                              O O H CH                                         223   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                           OH        O O H CH                                                                               155-158                                  224   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                           OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               93-95                                    __________________________________________________________________________

                                      TABLE 16                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2    R         W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     225   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                            ##STR163##                                                                              O O H CH                                                                               70-73                                    226   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                        OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               77-79                                    227   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                        OH        O O H CH                                                                               130-133                                  228   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                         ##STR164##                                                                              O O H CH                                         229   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                        OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                         230   CH.sub.3                                                                          COSC.sub.3 H.sub.7 -i                                                                     OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               105-108                                  231   CH.sub.3                                                                          COSC.sub.3 H.sub.7 -i                                                                     OH        O O H CH                                                                               160-163                                  232   CH.sub.3                                                                          COSC.sub.5 H.sub.11                                                                       OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               1.5621                                   233   CH.sub.3                                                                          COSC.sub.5 H.sub.11                                                                       OH        O O H CH                                                                               132-134                                  234   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                        OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               1.5665                                   235   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                        OH        O O H CH                                                                               127-130                                  236   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                         ##STR165##                                                                              O O H CH                                                                               104-106                                  237   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                     OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               75-77                                    238   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                     OH        O O H CH                                         239   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                      ##STR166##                                                                              O O H CH                                         240   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -t                                                                     OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                         241   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -t                                                                     OH        O O H CH                                                                               126-128                                  242   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -t                                                                      ##STR167##                                                                              O O H CH                                         243   CH.sub.3                                                                           ##STR168##                                                                               OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                         244   CH.sub.3                                                                           ##STR169##                                                                               OH        O O H CH                                         245   CH.sub.3                                                                           ##STR170##                                                                                ##STR171##                                                                              O O H CH                                         __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.1                                                                             R.sup.2    R         W X Yn                                                                               Z or (n.sub.D.sup.20)                    __________________________________________________________________________     246   CH.sub.3                                                                            CON(CH.sub.3).sub.2                                                                        ##STR172##                                                                              O O H CH                                                                               Unmeasurable                           247   CH.sub.3                                                                            CON(CH.sub.3).sub.2                                                                       OH        O O H CH                                                                               185-187                                248   CH.sub.3                                                                            CON(CH.sub.3).sub.2                                                                       OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               Unmeasurable                           249   CH.sub.3                                                                             ##STR173##                                                                                ##STR174##                                                                              O O H CH                                       250   CH.sub.3                                                                             ##STR175##                                                                               OH        O O H CH                                                                               171-174                                251   CH.sub.3                                                                             ##STR176##                                                                                ##STR177##                                                                              O O H CH                                       252   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                         ##STR178##                                                                              O O H CH                                       253   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                         ##STR179##                                                                              O O H CH                                       254   CH.sub.3                                                                            COCl       OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               75-78                                  255   CH.sub.3                                                                            COCl                                                                                       ##STR180##                                                                              O O H CH                                                                               136-140                                256   Cl   COOC.sub.2 H.sub.5                                                                        OH        O O H CH                                       257   COOC.sub.2 H.sub.5                                                                  Cl         OH        O O H CH                                       258   CH.sub.3                                                                             ##STR181##                                                                               OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               95-97                                  259   CH.sub.3                                                                             ##STR182##                                                                               OH        O O H CH                                                                               144.5-147                              260   CH.sub.3                                                                             ##STR183##                                                                                ##STR184##                                                                              O O H CH                                       __________________________________________________________________________

                                      TABLE 18                                     __________________________________________________________________________     Compound                               m.p. (°C.)                       No.   R.sup.1                                                                            R.sup.2    R         W X Yn                                                                               Z or (n.sub.D.sup.20)                     __________________________________________________________________________     261   CH.sub.3                                                                           COSCH.sub.2 CHCH.sub.2                                                                     ##STR185##                                                                              O O H CH                                        262   CH.sub.3                                                                           COSCH.sub.2 CHCH.sub.2                                                                    OH        O O H CH                                                                               1.5786                                  263   CH.sub.3                                                                           COSCH.sub.2 CHCH.sub.2                                                                     ##STR186##                                                                              O O H CH                                        264   CH.sub.3                                                                           COSCH.sub.2 CCH                                                                            ##STR187##                                                                              O O H CH                                        265   CH.sub.3                                                                           COSCH.sub.2 CCH                                                                           OH        O O H CH                                        266   CH.sub.3                                                                           COSCH.sub.2 CCH                                                                            ##STR188##                                                                              O O H CH                                        267   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                         ##STR189##                                                                              O O H CH                                                                               102.5-105                               268   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                        OH        O O H CH                                                                               140.5-144                               269   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                         ##STR190##                                                                              O O H CH                                                                               1.5291                                  270   C.sub.2 H.sub.5                                                                    COOCH.sub.3                                                                                ##STR191##                                                                              O O H CH                                                                               115-117                                 271   C.sub.2 H.sub.5                                                                    COOCH.sub.3                                                                               OH        O O H CH                                                                               164-167                                 272   C.sub.2 H.sub.5                                                                    COOH                                                                                       ##STR192##                                                                              O O H CH                                                                               185-188                                 273   C.sub.3 H.sub.7 -i                                                                 COOC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                         O O H CH                                                                               1.5459                                  274   C.sub.3 H.sub.7 -i                                                                 COOC.sub.2 H.sub.5                                                                        OH        O O H CH                                                                               157-159                                 275   C.sub.3 H.sub.7 -i                                                                 COOC.sub.2 H.sub.5                                                                         ##STR193##                                                                              O O H CH                                                                               1.5318                                  276   C.sub.2 H.sub.5                                                                    COOC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                         O O H CH                                                                               1.5490                                  277   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                         O O H CH                                                                               1.5431                                  __________________________________________________________________________

                                      TABLE 19                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2  R         W X Yn                                                                               Z or (n.sub.D.sup.20)                        __________________________________________________________________________     278   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Cl                                                                   OH        O O H CH                                                                               161-165                                    279   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Cl                                                                    ##STR194##                                                                              O O H CH                                                                               124-125                                    280   CH.sub.3                                                                          COOC.sub.2 H.sub.4 F                                                                    OH        O O H CH                                                                               152-155                                    281   CH.sub.3                                                                          COOC.sub.2 H.sub.4 F                                                                     ##STR195##                                                                              O O H CH                                                                               114-117                                    282   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Br                                                                    ##STR196##                                                                              O O H CH                                                                               124-127                                    283   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Br                                                                   OH        O O H CH                                           284   CH.sub.3                                                                           ##STR197##                                                                             OCH.sub.2 CCH.sub.2                                                                      O O H CH                                                                               138-140                                    285   H  COOCH.sub.3                                                                              ##STR198##                                                                              O O H CH                                           286   H  COOCH.sub.3                                                                             OH        O O H CH                                                                               150-153                                    287   H  COOCH.sub.3                                                                              ##STR199##                                                                              O O H CH                                           288   H  COOC.sub.3 H.sub.7                                                                       ##STR200##                                                                              O O H CH                                           289   H  COOC.sub.3 H.sub.7                                                                      OH        O O H CH                                                                               158-161                                    290   H  COOC.sub.3 H.sub.7                                                                       ##STR201##                                                                              O O H CH                                           291   H  COOC.sub.3 H.sub.7 -i                                                                    ##STR202##                                                                              O O H CH                                                                               80-82                                      292   H  COOC.sub.3 H.sub.7 -i                                                                   OH        O O H CH                                                                               140-143.5                                  293   H  COOC.sub.3 H.sub.7 -i                                                                    ##STR203##                                                                              O O H CH                                           __________________________________________________________________________

                                      TABLE 20                                     __________________________________________________________________________     Compound                        m.p. (°C.)                              No.   R.sup.1                                                                          R.sup.2                                                                              R         W X Yn                                                                               Z or (n.sub.D.sup.20)                            __________________________________________________________________________     294   H COOC.sub.4 H.sub.9                                                                    ##STR204##                                                                              O O H CH                                                                               82-84                                          295   H COOC.sub.4 H.sub.9                                                                   OH        O O H CH                                                                               134-137                                        296   H COOC.sub.4 H.sub.9                                                                    ##STR205##                                                                              O O H CH                                               297   H COOC.sub.4 H.sub.9 -i                                                                 ##STR206##                                                                              O O H CH                                                                               95-98                                          298   H COOC.sub.4 H.sub.9 -i                                                                OH        O O H CH                                                                               140-144                                        299   H COOC.sub.4 H.sub.9 -i                                                                 ##STR207##                                                                              O O H CH                                               300   H COOC.sub.4 H.sub.9 -s                                                                 ##STR208##                                                                              O O H CH                                                                               91-93                                          301   H COOC.sub.4 H.sub.9 -s                                                                OH        O O H CH                                                                               Unmeasurable                                   302   H COOC.sub.4 H.sub.9 -s                                                                 ##STR209##                                                                              O O H CH                                               303   H COOC.sub.4 H.sub.9 -t                                                                 ##STR210##                                                                              O O H CH                                               304   H COOC.sub.4 H.sub.9 -t                                                                OH        O O H CH                                               305   H COOC.sub.4 H.sub.9 -t                                                                 ##STR211##                                                                              O O H CH                                               306   H COOC.sub.5 H.sub.11                                                                   ##STR212##                                                                              O O H CH                                                                               88-90                                          307   H COOC.sub.5 H.sub.11                                                                  OH        O O H CH                                                                               117-119                                        308   H COOC.sub.5 H.sub.11                                                                   ##STR213##                                                                              O O H CH                                               __________________________________________________________________________

                                      TABLE 21                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2    R         W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     309   H  COOC.sub.6 H.sub.13                                                                        ##STR214##                                                                              O O H CH                                         310   H  COOC.sub.6 H.sub.13                                                                       OH        O O H CH                                         311   H  COOC.sub.6 H.sub.13                                                                        ##STR215##                                                                              O O H CH                                         312   H                                                                                  ##STR216##                                                                                ##STR217##                                                                              O O H CH                                         313   H                                                                                  ##STR218##                                                                               OH        O O H CH                                         314   H                                                                                  ##STR219##                                                                                ##STR220##                                                                              O O H CH                                         315   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                     ##STR221##                                                                              O O H CH                                                                               Unmeasurable                             316   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                    OH        O O H CH                                                                               173--176                                 317   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                    OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               157-159.5                                318   CH.sub.3                                                                           ##STR222##                                                                               OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               137-139                                  319   CH.sub.3                                                                           ##STR223##                                                                               OH        O O H CH                                                                               137-138                                  320   CH.sub.3                                                                           ##STR224##                                                                                ##STR225##                                                                              O O H CH                                         321   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                             ##STR226##                                                                              O O H CH                                                                               162-165                                  322   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                            OH        O O H CH                                                                               137-140                                  323   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                             ##STR227##                                                                              O O H CH                                         __________________________________________________________________________

                                      TABLE 22                                     __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.1                                                                           R.sup.2  R          W X Yn                                                                               Z or (n.sub.D.sup.20)                       __________________________________________________________________________     324   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                          OCH.sub.2 OC.sub.2 H.sub.5                                                                O O H CH                                          325   CH.sub.3                                                                           ##STR228##                                                                              ##STR229##                                                                               O O H CH                                                                               149-151                                   326   CH.sub.3                                                                           ##STR230##                                                                             OH         O O H CH                                                                               146-148                                   327   CH.sub.3                                                                           ##STR231##                                                                              ##STR232##                                                                               O O H CH                                                                               1.5330                                    328   CH.sub.3                                                                           ##STR233##                                                                             OCH.sub.2 OC.sub.2 H.sub.5                                                                O O H CH                                          329   CH.sub.3                                                                           ##STR234##                                                                             OH         O O H CH                                                                               173-175                                   330   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                      O.sup.-  Na.sup.+                                                                         O O H CH                                          331   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                       ##STR235##                                                                               O O H CH                                          332   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                      OCH.sub.2 CHCH.sub.2                                                                      O O H CH                                          333   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                       ##STR236##                                                                               O O H CH                                          334   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                      N(CH.sub.3).sub.2                                                                         O O H CH                                          335   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                       ##STR237##                                                                               O O H CH                                          336   CH.sub.3                                                                           ##STR238##                                                                              ##STR239##                                                                               O O H CH                                                                               Unmeasurable                              337   CH.sub.3                                                                           ##STR240##                                                                             OH         O O H CH                                                                               138-143                                   __________________________________________________________________________

                                      TABLE 23                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                             R.sup.2  R         W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     338   CH.sub.3                                                                             ##STR241##                                                                             OH        O O H CH                                         339   CH.sub.3                                                                            COOCH.sub.2 OC.sub.2 H.sub.5                                                             ##STR242##                                                                              O O H CH                                                                               110-113                                  340   CH.sub.3                                                                            COOCH.sub.2 OC.sub.2 H.sub.5                                                            OH        O O H CH                                                                               152-154                                  341   CH.sub.3                                                                            COOC.sub.2 H.sub.4 SCH.sub.3                                                            OH        O O H CH                                                                               140-143                                  342   CH.sub.3                                                                            COOC.sub.2 H.sub.4 SCH.sub.3                                                            OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               64-66                                    343   CH.sub.3                                                                            COOCH(CF.sub.3).sub.2                                                                    ##STR243##                                                                              O O H CH                                                                               158-160.5                                344   CH.sub.3                                                                            COOCH(CF.sub.3).sub.2                                                                   OH        O O H CH                                                                               137-140                                  345   CH.sub.3                                                                            COOCH.sub.3                                                                             O.sup.-  H.sub.3.sup.+ NCH(CH.sub.3).sub.2                                               O O H CH                                                                               133.5-137                                346   CH.sub.3                                                                             ##STR244##                                                                             OH        O O H CH                                                                               189-191                                  347   CH.sub.3                                                                            COOC.sub.2 H.sub.4 OCH.sub.3                                                             ##STR245##                                                                              O O H CH                                                                               105-107                                  348   CH.sub.3                                                                            COOC.sub.2 H.sub.4 OCH.sub.3                                                            OH        O O H CH                                                                               138-142                                  349   CH.sub.3                                                                            COOC.sub.2 H.sub.4 OCH.sub.3                                                             ##STR246##                                                                              O O H CH                                         350                                                                                   ##STR247##                                                                         COOCH.sub.3                                                                              ##STR248##                                                                              O O H CH                                         351                                                                                   ##STR249##                                                                         COOCH.sub.3                                                                             OH        O O H CH                                         352                                                                                   ##STR250##                                                                         COOCH.sub.3                                                                              ##STR251##                                                                              O O H CH                                         __________________________________________________________________________

                                      TABLE 24                                     __________________________________________________________________________     Compound                                    m.p. (°C.)                  No.   R.sup.1                                                                             R.sup.2        R         W X Yn                                                                               Z or (n.sub.D.sup.20)                __________________________________________________________________________     353                                                                                   ##STR252##                                                                         COOCH.sub.3    OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                   354   CH.sub.3                                                                            COOCH.sub.2 SCH.sub.3                                                                         OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               99-101                             355   CH.sub.3                                                                            COOCH.sub.2 SCH.sub.3                                                                         OH        O O H CH                                                                               152-155.5                          356   CH.sub.3                                                                            COOCH.sub.2 CF.sub.3                                                                          OH        O O H CH                                                                               152.5-155                          357   CH.sub.3                                                                            COOCH.sub.2 CF.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               114-116                            358   CH.sub.3                                                                            COOCH.sub.2 CF.sub.3                                                                           ##STR253##                                                                              O O H CH                                   359   CH.sub.3                                                                            COOH                                                                                           ##STR254##                                                                              O O H CH                                                                               222-225                            360   CH.sub.3                                                                            COC.sub.2 H.sub.5                                                                              ##STR255##                                                                              O O H CH                                   361   CH.sub.3                                                                            COC.sub.2 H.sub.5                                                                             OH        O O H CH                                   362   CH.sub.3                                                                            COC.sub.3 H.sub.7                                                                              ##STR256##                                                                              O O H CH                                   363   CH.sub.3                                                                            COC.sub.3 H.sub.7                                                                             OH        O O H CH                                   364   CH.sub.3                                                                            COC.sub.4 H.sub.9                                                                              ##STR257##                                                                              O O H CH                                                                               119-121                            365   CH.sub.3                                                                            COC.sub.4 H.sub.9                                                                             OH        O O H CH                                                                               136-138                            366   CH.sub.3                                                                            COC.sub.5 H.sub.11                                                                             ##STR258##                                                                              O O H CH                                                                               106-109                            367   CH.sub.3                                                                            COC.sub.5 H.sub.11                                                                            OH        O O H CH                                                                               130-132                            368   CH.sub.3                                                                             ##STR259##    OH        O O H CH                                                                               Unmeasurable                       369   CH.sub.3                                                                             ##STR260##                                                                                    ##STR261##                                                                              O O H CH                                                                               1.5519                             __________________________________________________________________________

                                      TABLE 25                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                              R.sup.2 R         W X Yn                                                                               Z or (n.sub.D.sup.20)                      __________________________________________________________________________     370   CH.sub.3                                                                             COOH                                                                                    ##STR262##                                                                              O O H CH                                                                               132-135                                  371   CH.sub.3                                                                             COOH    OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                                                               207-210                                  372   H     COOCH.sub.2 C.sub.4 H.sub.9 -t                                                         OH        O O H CH                                         373   H     COSC.sub.2 H.sub.5                                                                     OH        O O H CH                                         374   H     CONHC.sub.2 H.sub.5                                                                    OH        O O H CH                                         375   H     CON(CH.sub.3).sub.2                                                                    OH        O O H CH                                         376   H     COSC.sub.3 H.sub.7                                                                     OH        O O H CH                                         377   H     COSC.sub.4 H.sub.9                                                                     OH        O O H CH                                         378   CH.sub.3 OCH.sub.2                                                                   COOCH.sub.3                                                                             ##STR263##                                                                              O O H CH                                                                               92-95                                    379   CH.sub.3 OCH.sub.2                                                                   COOCH.sub.3                                                                            OH        O O H CH                                                                               150-153                                  380   CH.sub.3 OCH.sub.2                                                                   COOC.sub.2 H.sub.5                                                                      ##STR264##                                                                              O O H CH                                         381   CH.sub.3 OC.sub.2 H.sub.4                                                            COOCH.sub.3                                                                             ##STR265##                                                                              O O H CH                                         382   CH.sub.3 OC.sub.2 H.sub.4                                                            COOCH.sub.3                                                                            OH        O O H CH                                         383   CH.sub.3 OC.sub.2 H.sub.4                                                            COOCH.sub.3                                                                             ##STR266##                                                                              O O H CH                                         __________________________________________________________________________

                                      TABLE 26                                     __________________________________________________________________________      ##STR267##                                                                    Compound                          m.p. (°C.)                            No.   R.sup.2                                                                             R.sup.3                                                                            R.sup.4                                                                             R         W Z or (n.sub.D.sup.20)                          __________________________________________________________________________     384   COOCH.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                             ##STR268##                                                                              O CH                                                                               145-147                                      385   COOCH.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                            OH        O CH                                                                               174-177                                      386   COOCH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                           OH        O CH                                                                               138-140                                      387   COOCH.sub.3                                                                         CH.sub.3                                                                           Cl   OH        O CH                                             388   COOCH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                            ##STR269##                                                                              O CH                                                                               102.5-106                                    389   COOCH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                           OH        O N 143-146                                      390   COOCH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                            ##STR270##                                                                              O N 117-120                                      391   COOCH.sub.3                                                                         OCH.sub.3                                                                          Cl   OH        O CH                                                                               162-164                                      392   COOCH.sub.3                                                                         OCH.sub.3                                                                          NHCH.sub.3                                                                          OH        O CH                                             393   COOCH.sub.3                                                                         OCH.sub.3                                                                          OCHF.sub.2                                                                          OH        O CH                                                                               151-155                                      394   COOCH.sub.3                                                                         OCHF.sub.2                                                                         OCHF.sub.2                                                                          OH        O CH                                             395   COOCH.sub.3                                                                         OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   OH        O CH                                                                               167-170                                      396   COOCH.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                             ##STR271##                                                                              O N                                              397   COOCH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                            ##STR272##                                                                              O CH                                             398   COOCH.sub.3                                                                         Cl  OCH.sub.3                                                                            ##STR273##                                                                              O CH                                                                               129-132                                      __________________________________________________________________________

                                      TABLE 27                                     __________________________________________________________________________      ##STR274##                                                                    Compound                          m.p. (°C.)                            No.   R.sup.1                                                                             R.sup.2                                                                             R         W X   Z or (n.sub.D.sup.20)                          __________________________________________________________________________     399   H    H    H         O S   CH                                             400   H    H    OH        O S   CH                                             401   H    H                                                                                    ##STR275##                                                                              O S   CH                                             402   H    H    H         O NCH.sub.3                                                                          CH                                             403   H    H    OH        O NCH.sub.3                                                                          CH                                             404   H    H                                                                                    ##STR276##                                                                              O NCH.sub.3                                                                          CH                                             405   H    COOC.sub.2 H.sub.5                                                                  H         O O   CH                                                                               116-124                                      406   H    COOC.sub.2 H.sub.5                                                                  OH        O O   CH                                             407   H    COOC.sub.2 H.sub.5                                                                   ##STR277##                                                                              O O   CH                                             408   CH   COOC.sub.2 H.sub.5                                                                  H         O O   CH                                             409   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                  OH        O O   CH                                             410   H    COOC.sub.2 H.sub.5                                                                  OH        O NCH.sub.3                                                                          CH                                             411   H    COOC.sub.2 H.sub.5                                                                  OH        O S   CH                                             412   COOC.sub.2 H.sub.5                                                                  H    H         O O   CH                                             413   COOC.sub.2 H.sub.5                                                                  H    OH        O O   CH                                             414   COOC.sub.2 H.sub.5                                                                  H    H         O NCH.sub.3                                                                          CH                                             415   COOC.sub.2 H.sub.5                                                                  H    H         O NCH.sub.3                                                                          N                                              416   COOC.sub.2 H.sub.5                                                                  CH.sub.3                                                                            OH        O O   CH                                             417   COOC.sub.2 H.sub.5                                                                  H    OH        O NCH.sub.3                                                                          CH                                             418   COOC.sub.2 H.sub.5                                                                  H    H         O S   CH                                             419   COOC.sub.2 H.sub.5                                                                  H    OH        O S   CH                                             420   COOC.sub.2 H.sub.5                                                                  H    H         O S   CH                                             421   COOC.sub.2 H.sub.5                                                                  H    OH        O S   CH                                             422   H    CH.sub.3                                                                             ##STR278##                                                                              O NCH.sub.3                                                                          CH                                             __________________________________________________________________________

                                      TABLE 28                                     __________________________________________________________________________     Compound                          m.p. (°C.)                            No.   R.sup.1                                                                          R.sup.2                                                                           R       W X          Z or (n.sub.D.sup.20)                          __________________________________________________________________________     423   H CH.sub.3                                                                          OH      O NCH.sub.3  CH                                             424   H H  OCH.sub.2 OCH.sub.3                                                                    O NCH.sub.2 CHCH.sub.2                                                                      CH                                             425   H H  OH      O NCH.sub.2 CHCH.sub.2                                                                      CH                                             426   H CH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                                                    O NCH.sub.2 CHCH.sub.2                                                                      CH                                             427   H CH.sub.3                                                                          OH      O NCH.sub.2 CHCH.sub.2                                                                      CH                                             428   H CH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                   O NCH.sub.2 COOCH.sub.3                                                                     CH                                             429   H CH.sub.3                                                                          OH      O NCH.sub.2 COOCH.sub.3                                                                     CH                                             430   H CH.sub.3                                                                           ##STR279##                                                                            O NC(O)CH.sub.3                                                                             CH                                             431   H CH.sub.3                                                                          OH      O NC(O)CH.sub.3                                                                             CH                                             432   H CH.sub.3                                                                           ##STR280##                                                                            O                                                                                 ##STR281##                                                                               CH                                             433   H CH.sub.3                                                                          OH      O                                                                                 ##STR282##                                                                               CH                                             434   H CH.sub.3                                                                           ##STR283##                                                                            O NCOOC.sub.2 H.sub.5                                                                       CH                                             435   H CH.sub.3                                                                          OH      O NCOOC.sub.2 H.sub.5                                                                       CH                                             436   H CH.sub.3                                                                           ##STR284##                                                                            O                                                                                 ##STR285##                                                                               CH                                             437   H CH.sub.3                                                                          OH      O                                                                                 ##STR286##                                                                               CH                                             438   H CH.sub.3                                                                           ##STR287##                                                                            O                                                                                 ##STR288##                                                                               CH                                             439   H CH.sub.3                                                                          OH      O                                                                                 ##STR289##                                                                               CH                                             440   H CH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                   O NSO.sub.2 CH.sub.3                                                                        CH                                             441   H CH.sub.3                                                                          OH      O NSO.sub.2 CH.sub.3                                                                        CH                                             442   H CH.sub.3                                                                           ##STR290##                                                                            O NH         CH                                             443   H CH.sub.3                                                                          OH      O NH         CH                                             444   H CH.sub.3                                                                          OH      O NH         N                                              __________________________________________________________________________

                                      TABLE 29                                     __________________________________________________________________________      ##STR291##                                                                    Compound                         m.p. (°C.)                             No.   R.sup.1                                                                              R             W X  Z or (n.sub.D.sup.20)                           __________________________________________________________________________     445   H                                                                                     ##STR292##   O O  CH                                                                               Unmeasurable                                  446   H     OCH.sub.3     O O  CH                                                                               144-148                                       447   H     OH            O O  CH                                              448   H     OH            O O  N                                               449   H     OH            S O  CH                                              450   H     OH            S O  N                                               451   CH.sub.3                                                                             OH            O O  CH                                              452   C.sub.2 H.sub.5                                                                      OH            O O  CH                                              453                                                                                   ##STR293##                                                                          OH            O O  CH                                              454   H     OH            O NH CH                                              455   CH.sub.3                                                                             OH            O NH CH                                              456   H     OH            O NH N                                               457   H     OH            O S  CH                                              458   CH.sub.3                                                                             OH            O S  CH                                              459   H     OH            O S  N                                               460   CH.sub.3                                                                             OH            O S  N                                               __________________________________________________________________________

                                      TABLE 30                                     __________________________________________________________________________      ##STR294##                                                                    Compound                          m.p. (°C.)                            No.   R.sup.1                                                                              R.sup.3                                                                            R.sup.4                                                                            R       W X Z or (n.sub.D.sup.20)                          __________________________________________________________________________     461   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                       O O CH                                                                               111-114                                      462   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                              O O CH                                                                               125-127                                      463   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O O CH                                                                               168-174                                      464   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                              O O N 141-144                                      465   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O O N                                              466   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      S O CH                                             467   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      S O N                                              468   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                              O O CH                                                                               162-165                                      469   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O O CH                                                                               204-210                                      470   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O O N                                              471   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      S O CH                                             472   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    O O CH                                                                               1.5343                                       473   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OC.sub.2 H.sub.5                                                             O O N                                              474   C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O O CH                                             475                                                                                   ##STR295##                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O O CH                                                                               210-211                                      476   H     CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                              O O CH                                                                               1.5582                                       477   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OC.sub.2 H.sub.5                                                             O O CH                                                                               Unmeasurable                                 478   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O S CH                                             479   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O S CH                                             480   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O S N                                              481   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O S N                                              482   CH.sub.2 NO.sub.2                                                                    OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O S CH                                                                               168-169                                      483   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                                                      ##STR296##                                                                      O CH                                             __________________________________________________________________________

                  TABLE 31                                                         ______________________________________                                          ##STR297##                                                                    Com-                                                                           pound                                    m.p. (°C.)                     No.    R.sup.1 R        W    X      Z    or (n.sub.D.sup.20)                   ______________________________________                                         484    H       OH       O    O      CH                                         485    H       OH       S    O      CH                                         486    H       OH       O    O      N                                          487    CH.sub.3                                                                               OCH.sub.3                                                                               O    O      CH   167-171                               488    CH.sub.3                                                                               OH       O    O      CH   155-159                               489    CH.sub.3                                                                               OH       O    O      N                                          490    CH.sub.3                                                                               OH       S    O      N                                          491    CH.sub.3                                                                               OH       S    O      CH                                         492    H       OH       O    S      CH                                         493    H       OH       O    S      N                                          494    H       OH       O    NH     CH                                         495    H       OH       O    NCH.sub.3                                                                             CH                                         ______________________________________                                    

                  TABLE 32                                                         ______________________________________                                          ##STR298##                                                                                                                   m.p.                            Com-                                           (°C.)                    pound                                          or                              No.   R.sup.1                                                                               R.sup.3 R.sup.4                                                                              R    W   X      Z   (n.sub.D.sup.20)                ______________________________________                                         496   H      OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   O      CH                                  497   H      OCH.sub.3                                                                              OCH.sub.3                                                                            OH   S   O      CH                                  498   H      OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   NH     CH  169-                                                                           171                             499   CH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   O      CH                                  500   CH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   O      N                                   501   CH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            OH   S   O      N                                   502   CH.sub.3                                                                              CH.sub.3                                                                               CH.sub.3                                                                             OH   O   O      CH                                  503   CH.sub.3                                                                              CH.sub.3                                                                               OCH.sub.3                                                                            OH   O   O      CH                                  504   H      OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   S      CH                                  505   H      OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   S      N                                   506   H      OCH.sub.3                                                                              OCH.sub.3                                                                            OH   O   NCOCH.sub.3                                                                           CH  175-                                                                           178                             ______________________________________                                    

                  TABLE 33                                                         ______________________________________                                          ##STR299##                                                                    Com-                                                                           pound                                    m.p. (°C.)                     No.   R.sup.1 R.sup.2 R          W   Z   or (n.sub.D.sup.20)                   ______________________________________                                         507   OC.sub.2 H.sub.5                                                                       H       OCH.sub.3  O   CH  1.5243                                508   OC.sub.2 H.sub.5                                                                       H       OH         O   CH  1.5306                                509   CH.sub.3                                                                               H       OCH.sub.3  O   CH  1.5319                                510   CH.sub.3                                                                               H       OH         O   CH  Un-                                                                            measurable                            511   CH.sub.3                                                                               H       OCH.sub.3  O   N                                         512   CH.sub.3                                                                               H       OH         O   N                                         513   CH.sub.3                                                                               H       OCH.sub.3  S   CH                                        514   CH.sub.3                                                                               H       OH         S   CH                                        515   OC.sub.2 H.sub.5                                                                       H       OCH.sub.3  O   N                                         516   OC.sub.2 H.sub.5                                                                       H       OH         O   N                                         517   OC.sub.2 H.sub.5                                                                       H       OH         S   CH                                        518   OC.sub.2 H.sub.5                                                                       H       OH         S   N                                         519   OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                                ##STR300##                                                                               O   CH  1.5575                                520   OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                               OH         O   CH  105-109                               521   OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                                ##STR301##                                                                               O   CH                                        522   OC.sub.2 H.sub.5                                                                       CN                                                                                      ##STR302##                                                                               O   CH                                        523   OC.sub.2 H.sub.5                                                                       CN      OH         O   CH                                        524   OC.sub.2 H.sub.5                                                                       CN                                                                                      ##STR303##                                                                               O   CH                                        525   OC.sub.2 H.sub.5                                                                       COCH.sub.3                                                                              ##STR304##                                                                               O   CH                                        526   OC.sub.2 H.sub.5                                                                       COCH.sub.3                                                                             OH         O   CH                                        527   OC.sub.2 H.sub.5                                                                       COCH.sub.3                                                                              ##STR305##                                                                               O   CH                                        ______________________________________                                    

                                      TABLE 34                                     __________________________________________________________________________      ##STR306##                                                                    Com-                                                                           pound                            m.p. (°C.)                             No. R.sup.1                                                                           R.sup.2      R          X or (n.sub.D.sup.20)                           __________________________________________________________________________     528 CH.sub.3                                                                          COOC.sub.2 H.sub.4 SCH.sub.3                                                                OCH.sub.2 OCOC.sub.4 H.sub.9 -t                                                           O 69-71                                         529 CH.sub.3                                                                          COOH         OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 139-141                                       530 CH.sub.3                                                                          COOCH.sub.2 CHCHCH.sub.3                                                                    OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 1.5441                                        531 CH.sub.3                                                                          COOCH.sub.2 CHCHCl                                                                          OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O Unmeasurable                                  532 CH.sub.3                                                                          COOCH.sub.2 CClCHCl                                                                         OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 1.5488                                        533 CH.sub.3                                                                          COOCH.sub.2 CHCHCH.sub.3                                                                    OH         O 143-144                                       534 CH.sub.3                                                                          COOCH.sub.2 CHCHCl                                                                          OH         O 146-148                                       535 CH.sub.3                                                                          COOCH.sub.2 CClCHCl                                                                         OH         O 155-158                                       536 CH.sub.3                                                                           ##STR307##  OCH.sub.2 CHCH.sub.2                                                                      O 191-194                                       537 CH.sub.3                                                                           ##STR308##  OCH.sub.2 CHCH.sub.2                                                                      O 128-131                                       538 CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                      OCH.sub.2 OCOC.sub.4 H.sub.9 -t                                                           O 183-184.5                                     539 CH.sub.3                                                                          COSC.sub.5 H.sub.11                                                                         OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                        O 1.5380                                        540 CH.sub.3                                                                          COONC(CH.sub.3).sub.2                                                                       OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                        O 186-189                                       541 H  COOCH.sub.2 CHCH.sub.2                                                                       ##STR309##                                                                               O 85-87                                         542 H  COOH                                                                                         ##STR310##                                                                               O 174-175                                       543 CH.sub.3                                                                           ##STR311##  OCH.sub.2 CHCH.sub.2                                                                      O 114-116                                       544 CH.sub.3                                                                          CONHC.sub.4 H.sub.9                                                                         OCH.sub.2 CHCH.sub.2                                                                      O 148-150                                       545 CH.sub.3                                                                          COOCH.sub.2 C(CH.sub.3)CH.sub.2                                                             OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 1.5438                                        546 CH.sub.3                                                                          COOCH(CH.sub.3)CHCH.sub.2                                                                   OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 1.5373                                        547 CH.sub.3                                                                          COOCH.sub.2 CHC(CH.sub.3).sub.2                                                             OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 1.5461                                        548 CH.sub.3                                                                          COOCH.sub.2 C CCH.sub.3                                                                     OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 69-71                                         549 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 C CH                                                                   OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 66-68                                         550 CH.sub.3                                                                          COOCH(CH.sub.3)C CH                                                                         OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                      O 1.5420                                        551 CH.sub.3                                                                          COOCH(CH.sub.3)CHCH.sub.2                                                                   OH         O 140-144.5                                     __________________________________________________________________________

                                      TABLE 35                                     __________________________________________________________________________     Com-                                                                           pound                             m.p. (°C.)                            No. R.sup.1                                                                           R.sup.2       R          X or (n.sub.D.sup.20)                          __________________________________________________________________________     552 CH.sub.3                                                                          COOCH.sub.2 C CCH.sub.3                                                                      OH         O 174-178                                      553 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 C CH                                                                    OH         O Unmeasurable                                 554 CH.sub.3                                                                          COOCH(CH.sub.3)C CH                                                                          OH         O 160-165                                      555 CH.sub.3                                                                          COSCH(CH.sub.3)C.sub.2 H.sub.5                                                               OCH.sub.2 CHCH.sub.2                                                                      O 100-103                                      556 CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                           OCH(CH.sub.3)OCOC.sub.4 H.sub.9                                                           O 102-106                                      557 CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                           OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                        O 126-129                                      558 CH.sub.3                                                                          CONHC.sub.4 H.sub.9                                                                          OH         O 177-179                                      559 CH.sub.3                                                                          CON(CH.sub.3)C.sub.4 H.sub.9                                                                 OCH.sub.2 CHCH.sub.2                                                                      O 1.5465                                       560 CH.sub.3                                                                          CON(CH.sub.3)C.sub.4 H.sub.9                                                                 OH         O 162-166                                      561 CH.sub.3                                                                           ##STR312##   OCH.sub.2 CHCH.sub.2                                                                      O 218-220                                      562 CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                        OH         O 130-133                                      563 CH.sub.3                                                                           ##STR313##   OH         O 158-163                                      564 CH.sub.3                                                                          COOCH.sub.2 C CC.sub.2 H.sub.5                                                               OCH.sub.2 OCH.sub.3                                                                       O 95-97                                        565 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 C CCH.sub.3                                                             OCH.sub.2 OCH.sub.3                                                                       O 140.5-143                                    566 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 C CH                                                           OCH.sub.2 OCH.sub.3                                                                       O 78-81                                        567 CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 C CH                                                                 OCH.sub.2 OCH.sub.3                                                                       O 137-138.5                                    568 CH.sub.3                                                                          COOCH(C.sub.2 H.sub.5)C CH                                                                   OCH.sub.2 OCH.sub.3                                                                       O 138-140                                      569 CH.sub.3                                                                          COSCH.sub.2 CHCH.sub.2                                                                       OCH.sub.2 OCH.sub.3                                                                       O 1.5850                                       570 CH.sub.3                                                                          COOCH.sub.2 C CC.sub.2 H.sub.5                                                               OH         O 167-169                                      571 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 C CCH.sub.3                                                             OH         O Unmeasurable                                 572 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 C CH                                                           OH         O 160-161.5                                    573 CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 C CH                                                                 OH         O 133-135                                      574 CH.sub.3                                                                          COOCH(C.sub.2 H.sub.5)C CH                                                                   OH         O 155-156.5                                    575 C.sub.2 H.sub.5                                                                   COOH          OH         O 171-174.5                                    576 CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                           OCH(CH.sub.3)OCOC.sub.2 H.sub.5                                                           O 104.5-107                                    577 CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                           OCH(CH.sub.3)OCOC.sub.3 H.sub.7                                                           O 104-105.5                                    578 CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                           OCH(CH.sub.3)OCOC.sub.3 H.sub.7 -i                                                        O 123-126                                      579 CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                           OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -i                                                        O 124.5-126.5                                  __________________________________________________________________________

                                      TABLE 36                                     __________________________________________________________________________     Com-                                                                           pound                          m.p. (°C.)                               No. R.sup.1                                                                            R.sup.2    R        X  or (n.sub.D.sup.20)                             __________________________________________________________________________     580 CH.sub.3                                                                            ##STR314##                                                                               OCH.sub.2 CHCH.sub.2                                                                    O  97-99                                           581 CH.sub.3                                                                            ##STR315##                                                                               OH       O  110-114                                         582 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.2 CHCH.sub.2                                                                    O  99-101                                          583 CH.sub.3                                                                           COOCH.sub.2 CHCl.sub.2                                                                    OCH.sub.2 CHCH.sub.2                                                                    O  97-98                                           584 CH.sub.3                                                                           COOCH.sub.2 CCl.sub.3                                                                     OCH.sub.2 CHCH.sub.2                                                                    O  126-128.5                                       585 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 Cl                                                                   OH       O  155-157                                         586 CH.sub.3                                                                           COOCH.sub.2 CHCl.sub.2                                                                    OH       O  129-132                                         587 CH.sub.3                                                                           COOCH.sub.2 CCl.sub.3                                                                     OH       O  97-101                                          588 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 Br                                                                   OCH.sub.2 CHCH.sub.2                                                                    O  106-108                                         589 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 CN                                                                   OCH.sub.2 CHCH.sub.2                                                                    O  128-130                                         590 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 Br                                                                   OH       O  159-162                                         591 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 CN                                                                   OH       O  177-179.5                                       592 CH.sub.3                                                                           COOCH(CF.sub.3).sub.2                                                                     OCH.sub.2 CHCH.sub.2                                                                    O  139-141                                         593 CH.sub.3                                                                            ##STR316##                                                                               OCH.sub.2 CHCH.sub.2                                                                    O  85-89                                           594 CH.sub.3                                                                            ##STR317##                                                                               OCH.sub.2 CHCH.sub.2                                                                    O  98-101.5                                        595 CH.sub.3                                                                            ##STR318##                                                                               OH       O  160-162                                         596 CH.sub.3                                                                            ##STR319##                                                                               OH       O  155-158                                         597 CH.sub.3                                                                           COSCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                   OCH.sub.2 CHCH.sub.2                                                                    O  72-74                                           598 CH.sub.3                                                                           COSCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                   OH       O  99-101                                          599 CH.sub.3                                                                           COSCH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                             OCH.sub.2 CHCH.sub.2                                                                    O  68-69.5                                         600 CH.sub.3                                                                           COSCH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                             OH       O  139-142                                         601 H   COOCH.sub.2                                                                               OH       O  158-163                                         602 C.sub.2 H.sub.5                                                                     ##STR320##                                                                                ##STR321##                                                                             O  110-112                                         __________________________________________________________________________

                                      TABLE 37                                     __________________________________________________________________________     Com-                                                                           pound                          m.p. (°C.)                               No. R.sup.1                                                                            R.sup.2   R        X   or (n.sub.D.sup.20)                             __________________________________________________________________________     603 C.sub.2 H.sub.5                                                                    COC.sub.2 H.sub.5                                                                        OH       O   140.5-143                                       604 C.sub.4 H.sub.9                                                                    COCH.sub.3                                                                               OH       O   134-136                                         605 H                                                                                   ##STR322##                                                                              OCH.sub.2 CHCH.sub.2                                                                    O   100-103                                         606 CH.sub.3                                                                           H         OCH.sub.2 CHCH.sub.2                                                                    S   89-91                                           607 CH.sub.3                                                                           H         OH       S   151-155                                         608 CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                        ##STR323##                                                                             NCH.sub.3                                                                          151-156                                         609 CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                       OH       NCH.sub.3                                                                          200-202                                         610 CH.sub.3                                                                           COOC.sub.4 H.sub.9 -t                                                                     ##STR324##                                                                             NH  183-187                                         611 CH.sub.3                                                                           COOC.sub.4 H.sub.9 -t                                                                    OH       NH  187-190                                         612 CH.sub.3                                                                           H         OH       NH  167-170                                         613 CH.sub.3                                                                           COOCH.sub.3                                                                               ##STR325##                                                                             NH  164-166                                         614 CH.sub.3                                                                           COOCH.sub.3                                                                              OH       NH  194-197                                         615 CH.sub.3                                                                           COOCH.sub.2 CHCH.sub.2                                                                    ##STR326##                                                                             NH  204-208                                         616 CH.sub.3                                                                           COOH                                                                                      ##STR327##                                                                             NH  161-164                                         617 CH.sub.3                                                                           COOC.sub.3 H.sub.7                                                                       OH       NH  175-179                                         618 CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                    OH       NH  180-183                                         619 CH.sub.3                                                                           COOC.sub.4 H.sub.9                                                                       OH       NH  143-148                                         620 CH.sub.3                                                                           COOC.sub.4 H.sub.9 -i                                                                    OH       NH  140-146.5                                       621 CH.sub.3                                                                           COOC.sub.4 H.sub.9 -s                                                                    OH       NH  145-150                                         622 CH.sub.3                                                                           COOC.sub.5 H.sub.11                                                                      OH       NH  119-123                                         623 CH.sub.3                                                                           COOC.sub.6 H.sub.13                                                                      OH       NH  125-130                                         624 CH.sub.3                                                                           COOC.sub.3 H.sub.7                                                                        ##STR328##                                                                             NH  207-209                                         __________________________________________________________________________

                                      TABLE 38                                     __________________________________________________________________________     Com-                                                                           pound                          m.p. (°C.)                               No.  R.sup.1                                                                            R.sup.2  R        X   or (n.sub.D.sup.20)                             __________________________________________________________________________     625  CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                    ##STR329##                                                                             NH  203-205                                         626  CH.sub.3                                                                           COOC.sub.4 H.sub.9                                                                       ##STR330##                                                                             NH  191.5-194                                       627  CH.sub.3                                                                           COOC.sub.4 H.sub.9 -i                                                                    ##STR331##                                                                             NH  200-203                                         628  CH.sub.3                                                                           COOC.sub.4 H.sub.9 -s                                                                    ##STR332##                                                                             NH  170-173                                         629  CH.sub.3                                                                           COOC.sub.5 H.sub.11                                                                      ##STR333##                                                                             NH  137-139                                         630  CH.sub.3                                                                           COOC.sub.6 H.sub.13                                                                      ##STR334##                                                                             NH  130-133                                         631  CH.sub.3                                                                            ##STR335##                                                                              ##STR336##                                                                             NH  181-184                                         632  CH.sub.3                                                                            ##STR337##                                                                              ##STR338##                                                                             NH  192.5-196                                       633  CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 OCH.sub.3                                                           ##STR339##                                                                             NH  187-190                                         634  CH.sub.3                                                                           COCF.sub.3                                                                              OH       NH  162-167                                         635  CH.sub.3                                                                           COCF.sub.3                                                                               ##STR340##                                                                             NH  165-167                                         636  CH.sub.3                                                                            ##STR341##                                                                             OH       NH  223-227                                         637  CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 OCH.sub.3                                                          OH       NH  182-186                                         638  CH.sub.3                                                                           Cl       OH       NH  176-179                                         639  CH.sub.3                                                                           COC.sub.2 H.sub.5                                                                       OH       NH  192-195                                         640  CH.sub.3                                                                           COC.sub.2 H.sub.5                                                                        ##STR342##                                                                             NH  173-176                                         641  CH.sub.3                                                                           CN                                                                                       ##STR343##                                                                             NH  151-154                                         __________________________________________________________________________

                                      TABLE 39                                     __________________________________________________________________________     Com-                                                                           pound                          m.p. (°C.)                               No. R.sup.1                                                                            R.sup.2   R        X   or (n.sub.D.sup.20)                             __________________________________________________________________________     642 CH.sub.3                                                                           COCH.sub.3                                                                               OH       NH  198-203                                         643 CH.sub.3                                                                           COCH.sub.3                                                                                ##STR344##                                                                             NH  206-211                                         644 CH.sub.3                                                                           CN                                                                                        ##STR345##                                                                             O   156-158                                         645 CH.sub.3                                                                           Br        OH       S   178-180                                         646 CH.sub.3                                                                           Br        OCH.sub.2 C(Br)CH.sub.2                                                                 S   126-128                                         647 CH.sub.3                                                                           Br        OCH.sub.2 CHCH.sub.2                                                                    S                                                   648 CH.sub.3                                                                           COC.sub.3 H.sub.7                                                                         ##STR346##                                                                             NH                                                  649 CH.sub.3                                                                           COC.sub.3 H.sub.7                                                                        OH       NH  193-196                                         650 CH.sub.3                                                                           CH.sub.2 CHCH.sub.2                                                                      OH       NH  130-134                                         651 CH.sub.3                                                                           C.sub.3 H.sub.7                                                                          OH       NH  137-142                                         652 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 F                                                                   OH       NH  193-195                                         653 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 Cl                                                                  OH       NH  203-205                                         654 CH.sub.3                                                                           COOCH(CH.sub.3)CH.sub.2 Cl                                                               OH       O   143-147                                         655 CH.sub.3                                                                           COOCH(CH.sub.2 Cl).sub.2                                                                 OH       O   115-119                                         656 CH.sub.3                                                                           COOCH(CH.sub.3)CH2F                                                                      OH       O   150-153                                         657 CH.sub.3                                                                           COOCH(CH.sub.3)CF.sub.3                                                                  OH       O   125-128                                         658 CH.sub.3                                                                           COOCH.sub.2 CHF.sub.2                                                                    OH       O   144-147                                         659 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 CH.sub.2 F                                                          OH       O   153-156                                         660 CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 OH                                                                  OH       O   148-151                                         661 CH.sub.3                                                                           COOCH.sub.2 COOC.sub.2 H.sub.5                                                           OH       O   130-133                                         662 CH.sub.3                                                                            ##STR347##                                                                              OH       O   154-157                                         663 CH.sub.3                                                                           CON(C.sub.2 H.sub.5).sub.2                                                               OH       NH  151-155                                         __________________________________________________________________________

                                      TABLE 40                                     __________________________________________________________________________      ##STR348##                                                                    Com-                                                                           pound                          m.p. (°C.)                               No.  R.sup.2   R        X  W Z or (n.sub.D.sup.20)                             __________________________________________________________________________     664  H                                                                                         ##STR349##                                                                             NH O CH                                                                               135-139                                         665  H         OH       NH O CH                                                                               167-170                                         666  CH.sub.2 CHCH.sub.2                                                                      OCH.sub.3                                                                               NH O CH                                                667  CH.sub.2 CHCH.sub.2                                                                      OH       NH O CH                                                                               130-134                                         668  CH.sub.2 C CH                                                                            OCH3     NH O CH                                                669  CH.sub.2 C CH                                                                            OH       NH O CH                                                670  CH.sub.2 CN                                                                              OCH3     NH O CH                                                671  CH.sub.2 CN                                                                              OH       NH O CH                                                                               165-169                                         672  CH.sub.2 COOCH.sub.3                                                                      ##STR350##                                                                             NH O CH                                                673  CH.sub.2 COOCH.sub.3                                                                     OH       NH O CH                                                674  CH.sub.2 N(CH.sub.3).sub.2                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                675  CH.sub.2 N(CH.sub.3).sub.2                                                               OH       NH O CH                                                676  CHCHCN    OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                677  CHCHCN    OH       NH O CH                                                678  CHCHNO.sub.2                                                                             OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                679  CHCHNO.sub.2                                                                             OH       NH O CH                                                680  CHO                                                                                       ##STR351##                                                                             NH O CH                                                                               148-149                                         681  CHO       OH       NH O CH                                                                               201-206                                         682  CHNC.sub.3 H.sub.7 -i                                                                    OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                683  CHNC.sub.3 H.sub.7 -i                                                                    OH       NH O CH                                                684                                                                                  ##STR352##                                                                              OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                __________________________________________________________________________

                                      TABLE 41                                     __________________________________________________________________________     Com-                                                                           pound                              m.p. (°C.)                           No. R.sup.2     R           X  W Z or (n.sub.D.sup.20)                         __________________________________________________________________________     685                                                                                 ##STR353## OH          NH O CH                                            686                                                                                 ##STR354##                                                                                 ##STR355## NH O CH                                            687                                                                                 ##STR356## OH          NH O CH                                            688 CHNN(CH.sub.3).sub.2                                                                        ##STR357## NH O CH                                            689 CHNN(CH.sub.3).sub.2                                                                       OH          NH O CH                                            690 CHNOH                                                                                       ##STR358## NH O CH                                            691 CHNOH       OH          NH O CH                                                                               165-170                                     692 CHNOCH.sub.3                                                                                ##STR359## NH O CH                                                                               131-133                                     693 CHNOCH.sub.3                                                                               OH          NH O CH                                                                               171-175                                     694 H           OH          NH O N 152-154                                     695 CHNOCH.sub.3                                                                               OH          NH O N                                             696 CHNOCH.sub.3                                                                               OCH.sub.3   NH S CH                                            697 CHNOCH.sub.3                                                                               OH          NH S CH                                            698 CHNOCH.sub.3                                                                               OCH.sub.2 C CH                                                                             NH O CH                                            699 CHNOCH.sub.3                                                                               OCH.sub.2 OCH.sub.3                                                                        NH O CH                                            700 CHNOCH.sub.3                                                                               OCH(CH.sub.3)OC(O)C.sub.4 H.sub.9 -t                                                       NH O CH                                            701 CHNOCH.sub.3                                                                                ##STR360## NH O CH                                            702 CHNOCH.sub.3                                                                               ONC(CH.sub.3).sub.2                                                                        NH O CH                                            703 CHNOCH.sub.3                                                                               SCH.sub.3   NH O CH                                            704 CHNOCH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                                                                       NH O CH                                            705 CHNOCH.sub.3                                                                               SCH.sub.2 C CH                                                                             NH O CH                                            __________________________________________________________________________

                                      TABLE 42                                     __________________________________________________________________________     Com-                                                                           pound                             m.p. (°C.)                            No. R.sup.1       R        X  W Z or (n.sub.D.sup.20)                          __________________________________________________________________________     706 CHNOCH.sub.3                                                                                  ##STR361##                                                                             NH O CH                                             707 CHNOCH.sub.3  NHC.sub.2 H.sub.5                                                                       NH O CH                                             708 CHNOCH.sub.3                                                                                  ##STR362##                                                                             NH O CH                                             709 CHNOCH.sub.3  NHSO.sub.2 CH.sub.3                                                                     NH O CH                                             710 CHNOCH.sub.3                                                                                  ##STR363##                                                                             NH O CH                                             711 CHNOCH.sub.3                                                                                  ##STR364##                                                                             NH O CH                                             712 CHNOCH.sub.3                                                                                  ##STR365##                                                                             NH O CH                                             713 CHNOC.sub.3 H.sub.7 -i                                                                        ##STR366##                                                                             NH O CH                                             714 CHNOC.sub.3 H.sub.7 -i                                                                       OH       NH O CH                                                                               123-127                                      715 CHNOCH.sub.2 CHCH.sub.2                                                                      OH       NH O CH                                             716 CHNOCH.sub.2 C CH                                                                            OH       NH O CH                                             717                                                                                 ##STR367##   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                             718                                                                                 ##STR368##   OH       NH O CH                                             719                                                                                 ##STR369##   OCH.sub.3                                                                               NH O CH                                             720                                                                                 ##STR370##   OH       NH O CH                                             721 COOC.sub.2 H.sub.5                                                                            ##STR371##                                                                             NH O CH                                                                               196-199                                      722 NH.sub.2      OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                                               132-135                                      __________________________________________________________________________

                                      TABLE 43                                     __________________________________________________________________________     Com-                                                                           pound                          m.p. (°C.)                               No. R.sup.2    R        X  W Z or (n.sub.D.sup.20)                             __________________________________________________________________________     723 NH.sub.2                                                                                   ##STR372##                                                                             NH O CH                                                724 NH.sub.2   OH       NH O CH                                                725 NHCH.sub.3                                                                                 ##STR373##                                                                             NH O CH                                                726 NHCH.sub.3 OH       NH O CH                                                727                                                                                 ##STR374##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                728                                                                                 ##STR375##                                                                               OH       NH O CH                                                729                                                                                 ##STR376##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                730                                                                                 ##STR377##                                                                               OH       NH O CH                                                731 N(CH.sub.3).sub.2                                                                          ##STR378##                                                                             NH O CH                                                732 N(CH.sub.3).sub.2                                                                         OH       NH O CH                                                733                                                                                 ##STR379##                                                                                ##STR380##                                                                             NH O CH                                                734                                                                                 ##STR381##                                                                               OH       NH O CH                                                735 NHC(O)CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                                               177-180                                         736 NHC(O)CH.sub.3                                                                            OH       NH O CH                                                                               230-233                                         737                                                                                 ##STR382##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                738                                                                                 ##STR383##                                                                               OH       NH O CH                                                                               168-172                                         739 NHCOOC.sub.2 H.sub.5                                                                      OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                740 NHCOOC.sub.2 H.sub.5                                                                      OH       NH O CH                                                                               177-179                                         __________________________________________________________________________

                                      TABLE 44                                     __________________________________________________________________________     Com-                                                                           pound                            m.p. (°C.)                             No. R.sup.2      R        X  W Z or (n.sub.D.sup.20)                           __________________________________________________________________________     741 NHC(O)SC.sub.2 H.sub.5                                                                      OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              742 NHC(O)SC.sub.2 H.sub.5                                                                      OH       NH O CH                                              743                                                                                 ##STR384##  OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              744                                                                                 ##STR385##  OH       NH O CH                                              745 NHC(O)NHCH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              746 NHC(O)NHCH.sub.3                                                                            OH       NH O CH                                              747 NHC(O)N(CH.sub.3).sub.2                                                                      ##STR386##                                                                             NH O CH                                              748 NHC(O)N(CH.sub.3).sub.2                                                                     OH       NH O CH                                              749 NHSO.sub.2 CH.sub.3                                                                         OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              750 NHSO.sub.2 CH.sub.3                                                                         OH       NH O CH                                              751                                                                                 ##STR387##  OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              752                                                                                 ##STR388##  OH       NH O CH                                              753 NCHCH.sub.3  OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              754 NCHCH.sub.3  OH       NH O CH                                              755                                                                                 ##STR389##  OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              756                                                                                 ##STR390##  OH       NH O CH                                                                               265-270                                       757                                                                                 ##STR391##  OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              758                                                                                 ##STR392##  OH       NH O CH                                              759 NO.sub.2     OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                                                               155-159                                       760 NO.sub.2     OH       NH O CH                                                                               >300° C.                               __________________________________________________________________________

                                      TABLE 45                                     __________________________________________________________________________     Com-                                                                           pound                              m.p. (°C.)                           No. R.sup.2                                                                             R        X         W    Z or (n.sub.D.sup.20)                         __________________________________________________________________________     761 NO.sub.2                                                                            OCH.sub.2 CHCH.sub.2                                                                    NCH.sub.3 O    CH                                            762 NO.sub.2                                                                            OH       NCH.sub.3 O    CH                                            763 COOC.sub.2 H.sub.5                                                                   ##STR393##                                                                             NCH.sub.2 CHCH.sub.2                                                                     O    CH                                                                               1.5774                                      764 COOC.sub.2 H.sub.5                                                                  OH       NCH.sub.2 CHCH.sub.2                                                                     O    CH                                            765 NH.sub.2                                                                             ##STR394##                                                                             NCH.sub.2 CHCH.sub.2                                                                     O    CH                                            766 NH.sub.2                                                                            OH       NCH.sub.2 CHCH.sub.2                                                                     O    CH                                                                               215-220                                     767 H    OCH.sub.2 OCH.sub.3                                                                     NCH.sub.2 C CH                                                                           O    CH                                            768 H    OH       NCH.sub.2 C CH                                                                           O    CH                                            769 COOC.sub.2 H.sub.5                                                                  OCH.sub.3                                                                               NCH.sub.2 OCH.sub.3                                                                      O    CH                                            770 COOC.sub.2 H.sub.5                                                                  OH       NCH.sub.2 OCH.sub.3                                                                      O    CH                                                                               158-162                                     771 COOC.sub.2 H.sub.5                                                                   ##STR395##                                                                             NCH.sub.2 OC(O)C.sub.4 H.sub.9 -t                                                        O    CH                                                                               182-183.5                                   772 COOC.sub.2 H.sub.5                                                                  OH       NCH.sub.2 OC(O)C.sub.4 H.sub.9 -t                                                        O    CH                                                                               193-195                                     773 COOC.sub.2 H.sub.5                                                                   ##STR396##                                                                             NCH.sub.2 COOC.sub.2 H.sub.5                                                             O    CH                                                                               141-143.5                                   774 COOC.sub.2 H.sub.5                                                                  OH       NCH.sub.2 COOC.sub.2 H.sub.5                                                             O    CH                                                                               190-193                                     775 H    OH       NC(O)CH.sub.3                                                                            O    CH                                            776 H    OH       NC(O)CH.sub.3                                                                            CH.sub.2                                                                            CH                                            777 H    OH       NC(O)CH.sub.3                                                                            CH(CN)                                                                              CH                                            778 H    OH       NC(O)CH.sub.3                                                                            C(O) CH                                            779 H    OCH.sub.3                                                                               NC(O)CH.sub.3                                                                            N(CHO)                                                                              CH                                            780 Cl   OCH.sub.2 OCH.sub.3                                                                     NC(O)CH.sub.3                                                                            O    CH                                            781 Cl   OH       NC(O)CH.sub.3                                                                            O    CH                                            782 OCH.sub.3                                                                            ##STR397##                                                                             NC(O)CH.sub.3                                                                            O    CH                                            __________________________________________________________________________

                                      TABLE 46                                     __________________________________________________________________________     Com-                                                                           pound                                 m.p. (°C.)                        No. R.sup.2    R        X         W Z or (n.sub.D.sup.20)                      __________________________________________________________________________     783 OCH.sub.3  OH       NC(O)CH.sub.3                                                                            O CH                                         784                                                                                 ##STR398##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NC(O)CH.sub.3                                                                            O CH                                         785                                                                                 ##STR399##                                                                               OH       NC(O)CH.sub.3                                                                            O CH                                         786 COOCH.sub.3                                                                                ##STR400##                                                                             NC(O)CH.sub.3                                                                            O CH                                                                               133-135                                  787 COOCH.sub.3                                                                               OH       NC(O)CH.sub.3                                                                            O CH                                                                               186-189                                  788 COOC.sub.2 H.sub.5                                                                         ##STR401##                                                                             NC(O)CH.sub.3                                                                            O CH                                                                               128-130.5                                789 COOC.sub.2 H.sub.5                                                                        OH       NC(O)CH.sub.3                                                                            O CH                                                                               174-177                                  790 COOCH.sub.2 CHCH.sub.2                                                                    OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     NC(O)CH.sub.3                                                                            O CH                                         791 COOCH.sub.2 CHCH.sub.2                                                                    OH       NC(O)CH.sub.3                                                                            O CH                                         792 COOCH.sub.2 C CH                                                                          OCH.sub.2 OCH.sub.3                                                                     NC(O)CH.sub.3                                                                            O CH                                         793 COOCH.sub.2 C CH                                                                          OH       NC(O)CH.sub.3                                                                            O CH                                         794 C(O)SCH.sub.3                                                                             OCH.sub.3                                                                               NC(O)CH.sub.3                                                                            O CH                                         795 C(O)SCH.sub.3                                                                             OH       NC(O)CH.sub.3                                                                            O CH                                         796 COOC.sub.2 H.sub.5                                                                         ##STR402##                                                                              ##STR403##                                                                              O CH                                                                               128-132.5                                797 COOC.sub.2 H.sub.5                                                                        OH                                                                                       ##STR404##                                                                              O CH                                                                               113-115                                  798                                                                                 ##STR405##                                                                               OCH.sub.2 OCH.sub.3                                                                      ##STR406##                                                                              O CH                                         799                                                                                 ##STR407##                                                                               OH                                                                                       ##STR408##                                                                              O CH                                         __________________________________________________________________________

                                      TABLE 47                                     __________________________________________________________________________     Com-                                                                           pound                                    m.p. (°C.)                     No. R.sup.2     R        X           W Z or (n.sub.D.sup.20)                   __________________________________________________________________________     800                                                                                 ##STR409##                                                                                 ##STR410##                                                                              ##STR411## O CH                                      801                                                                                 ##STR412## OH                                                                                       ##STR413## O CH                                      802 C(O)SCH.sub.2 CHCH.sub.2                                                                   OCH.sub.2 CHCH.sub.2                                                                     ##STR414## O CH                                      803 C(O)SCH.sub.2 CHCH.sub.2                                                                   OH                                                                                       ##STR415## O CH                                      804 C(O)SCH.sub.2 C CH                                                                         OCH.sub.2 CHCH.sub.2                                                                     ##STR416## O CH                                      805 C(O)SCH.sub.2 C CH                                                                         OH                                                                                       ##STR417## O CH                                      806 C(O)CH.sub.3                                                                                ##STR418##                                                                              ##STR419## O CH                                      807 C(O)CH.sub.3                                                                               OH                                                                                       ##STR420## O CH                                      808                                                                                 ##STR421## OH                                                                                       ##STR422## O CH                                      809                                                                                 ##STR423## OH                                                                                       ##STR424## O CH                                      810                                                                                 ##STR425## OH                                                                                       ##STR426## O CH                                      811 H           OH                                                                                       ##STR427## O CH                                      812 COOC.sub.2 H.sub.5                                                                          ##STR428##                                                                             NCOOC.sub.2 H.sub.5                                                                        O CH                                                                               105-108                               813 COOC.sub.2 H.sub.5                                                                         OH       NCOOC.sub.2 H.sub.5                                                                        O CH                                                                               170-173                               814 COOC.sub.2 H.sub.5                                                                          ##STR429##                                                                             NCOOC.sub.4 H.sub.9 -t                                                                     O CH                                                                               1.5649                                815 COOC.sub.2 H.sub.5                                                                         OH       NCOOC.sub.4 H.sub.9 -t                                                                     O CH                                                                               138-142                               __________________________________________________________________________

                                      TABLE 48                                     __________________________________________________________________________     Com-                                                                           pound                             m.p. (°C.)                            No. R.sup.2                                                                             R        X           W Z or (n.sub.D.sup.20)                          __________________________________________________________________________     816 H    OCH.sub.2 CHCH.sub.2                                                                     ##STR430## O CH                                             817 H    OH                                                                                       ##STR431## O CH                                             818 H                                                                                    ##STR432##                                                                              ##STR433## O CH                                             819 H    OH                                                                                       ##STR434## O CH                                             820 H    OCH.sub.2 CHCH.sub.2                                                                    NC(O)SCH.sub.3                                                                             O CH                                             821 H    OH       NC(O)SCH.sub.3                                                                             O CH                                             822 H    OCH.sub.2 CHCH.sub.2                                                                     ##STR435## O CH                                             823 H    OH                                                                                       ##STR436## O CH                                             824 COOC.sub.2 H.sub.5                                                                   ##STR437##                                                                             NC(O)N(CH.sub.3).sub.2                                                                     O CH                                                                               1.5767                                       825 COOC.sub.2 H.sub.5                                                                  OH       NC(O)N(CH.sub.3).sub.2                                                                     O CH                                                                               172-174                                      826 COOC.sub.2 H.sub.5                                                                   ##STR438##                                                                             NSO.sub.2 CH.sub.3                                                                         O CH                                                                               140.5-145                                    827 COOC.sub.2 H.sub.5                                                                  OH       NSO.sub.2 CH.sub.3                                                                         O CH                                                                               186-188                                      828 COOC.sub.2 H.sub.5                                                                   ##STR439##                                                                              ##STR440## O CH                                                                               Unmeasurable                                 829 COOC.sub.2 H.sub.5                                                                  OH                                                                                       ##STR441## O CH                                                                               149-152                                      830 COOC.sub.2 H.sub.5                                                                   ##STR442##                                                                             NSi(CH.sub.3).sub.2 C.sub.4 H.sub.9 -t                                                     O CH                                                                               Unmeasurable                                 831 COOC.sub.2 H.sub.5                                                                  OH       NSi(CH.sub.3).sub.2 C.sub.4 H.sub.9 -t                                                     O CH                                                                               175-178                                      832 COOC.sub.2 H.sub.5                                                                   ##STR443##                                                                             NSCCl.sub.3 O CH                                                                               173-177                                      __________________________________________________________________________

                                      TABLE 49                                     __________________________________________________________________________     Com-                                                                           pound                           m.p. (°C.)                              No. R.sup.2                                                                             R        X         W Z or (n.sub.D.sup.20)                            __________________________________________________________________________     833 COOC.sub.2 H.sub.5                                                                  OH       NSCCl.sub.3                                                                              O CH                                               834 H    OCH.sub.3                                                                                ##STR444##                                                                              O CH                                                                               187-190                                        835 H    OH                                                                                       ##STR445##                                                                              O CH                                                                               182-183.5                                      836 CN                                                                                   ##STR446##                                                                              ##STR447##                                                                              O CH                                                                               176-177                                        837 H                                                                                    ##STR448##                                                                             NC(O)CH.sub.3                                                                            O CH                                               838 H    OH       NC(O)CH.sub.3                                                                            O CH                                               839 H    OCH.sub.2 CHCH.sub.2                                                                    NC(O)CH.sub.3                                                                            O CH                                               840 H    OH       NC(O)CH.sub.3                                                                            O CH                                               841 H    OH       NC(O)CH.sub.3                                                                            O CH                                               __________________________________________________________________________

                                      TABLE 50                                     __________________________________________________________________________      ##STR449##                                                                    Com-                                                                           pound                                m.p. (°C.)                         No. R.sup.1                                                                           R.sup.2                                                                               R.sup.3                                                                             R.sup.4                                                                            R  X      W Z or (n.sub.D.sup.20)                       __________________________________________________________________________     842 CH.sub.3                                                                          H      CH.sub.3                                                                            CH.sub.3                                                                           OH NH     O CH                                                                               184-186                                   843 CH.sub.3                                                                          CHNOCH.sub.3                                                                          CH.sub.3                                                                            CH.sub.3                                                                           OH NH     O CH                                          844 CH.sub.3                                                                          H      N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OH NH     O CH                                                                               164-167                                   845 CH.sub.3                                                                          H      NHCH.sub.3                                                                          OCH.sub.3                                                                          OH NC(O)CH.sub.3                                                                         O CH                                          846 CF.sub.3                                                                          H      OCH.sub.3                                                                           OCH.sub.3                                                                          OH NC(O)CH.sub.3                                                                         O CH                                          __________________________________________________________________________

                                      TABLE 51                                     __________________________________________________________________________      ##STR450##                                                                    Com-                                                                           pound                            m.p. (°C.)                             No. X.sup.1                                                                           Q.sup.1     X.sup.2                                                                              R       or (n.sub.D.sup.20)                           __________________________________________________________________________     847 CH.sub.2                                                                          CH.sub.2    CO    OCH.sub.3                                                                              150-153                                       848 CH.sub.2                                                                          CH.sub.2    CO    OH      181.5-184                                     849 CH.sub.2                                                                          CH.sub.2    CNOCH.sub.3                                                                          OCH.sub.3                                                                              152-154                                       850 CH.sub.2                                                                          CH.sub.2    CNOCH.sub.3                                                                          OH                                                    851 CH.sub.2                                                                          CH.sub.2    CHOH  OCH.sub.3                                                                              135-137                                       852 CH.sub.2                                                                          CH.sub.2    CHOH  OH      151-153.5                                     853 NH CO          O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    Unmeasurable                                  854 NH CO          O     OH      188-189                                       855 NH CO          NH    OCH.sub.3                                             856 NH CO          NH    OH                                                    857 NH CC(CN)COOCH.sub.3                                                                          O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    100-105                                       858 NH CC(CN)COOCH.sub.3                                                                          O     OH      250-260                                       859 NH CC(CN).sub.2                                                                               O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    185-187                                       860 NH CC(CN).sub.2                                                                               O     O.sup.- N.sup.+ (C.sub.4 H.sub.9).sub.4                                                125-130                                       861 NH                                                                                 ##STR451## O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                   862 NH                                                                                 ##STR452## O     OH                                                    863 NH                                                                                 ##STR453## O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                   864 NH                                                                                 ##STR454## O     OH                                                    865 O  CO          S     OCH.sub.3                                                                              138-139                                       866 O  CO          S     OH                                                    __________________________________________________________________________

                                      TABLE 52                                     __________________________________________________________________________      ##STR455##                                                                    Com-                                                                           pound                             m.p. (°C.)                            No. X.sup.1                                                                            Q.sup.2                                                                             Q.sup.3                                                                              X.sup.2                                                                              R        or (n.sub.D.sup.20)                          __________________________________________________________________________     867 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CO    OCH.sub.3                                                                               185-187                                      868 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CO    OH       183-189                                      869 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CNOCH.sub.3                                                                          OCH.sub.3                                                                               128-131                                      870 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CNOCH.sub.3                                                                          OH                                                    871 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CHOH  OCH.sub.3                                             872 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CHOH  OH       147.5-149                                    873 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CH.sub.2                                                                              ##STR456##                                                                             1.5332                                       874 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CH.sub.2                                                                             OCH.sub.3                                                                               127-128                                      875 CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CH.sub.2                                                                             OH       141-147                                      876 CH.sub.2                                                                           CH.sub.2                                                                            C(CH.sub.3).sub.2                                                                    O     OCH.sub.3                                             877 CH.sub.2                                                                           CH.sub.2                                                                            C(CH.sub.3).sub.2                                                                    O     OH       151-153                                      878 NH  CO   CH.sub.2                                                                             O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     148-150                                      879 NH  CO   CH.sub.2                                                                             O     OH       200-202                                      880 NCH.sub.3                                                                          CO   CH.sub.2                                                                             O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     Unmeasurable                                 881 NCH.sub.3                                                                          CO   CH.sub.2                                                                             O     OH       178-180                                      882 NH  CO   CH(C.sub.2 H.sub.5)                                                                  O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     Unmeasurable                                 883 NH  CO   CH(C.sub.2 H.sub.5)                                                                  O     OH       195-197                                      884 NH  CH.sub.2                                                                            CH.sub.2                                                                             O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     1.5333                                       885 NH  CH.sub.2                                                                            CH.sub.2                                                                             O     OH       160-164                                      886 NH  CH.sub.2                                                                            CH.sub.2                                                                             S     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     Unmeasurable                                 887 NH  CH.sub.2                                                                            CH.sub.2                                                                             S     OH       164-166                                      888 NH  CH.sub.2                                                                            CH.sub.2                                                                             NH    OCH.sub.3                                             889 NH  CH.sub.2                                                                            CH.sub.2                                                                             NH    OH                                                    890 NH  CH(CH.sub.3)                                                                        CH.sub.2                                                                             O     OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     Unmeasurable                                 891 NH  CH(CH.sub.3)                                                                        CH.sub.2                                                                             O     OH       174-175                                      892 NH  CH.sub.2                                                                            CH(CH.sub.3)                                                                         O     OH       110-115                                      893 NH  CH.sub.2                                                                            CH(C.sub.2 H.sub.5)                                                                  O     OH                                                    __________________________________________________________________________

                                      TABLE 53                                     __________________________________________________________________________     Com-                                                                           pound                        m.p. (°C.)                                 No. X.sup.1                                                                           Q.sup.2                                                                           Q.sup.3  X.sup.2                                                                          R       or (n.sub.D.sup.20)                               __________________________________________________________________________     894 NH CH.sub.2                                                                          C(CH.sub.3).sub.2                                                                       O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                       895 NH CH.sub.2                                                                          C(CH.sub.3).sub.2                                                                       O OH                                                        896 NH CH.sub.2                                                                          CCH.sub.2                                                                               O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    Unmeasurable                                      897 NH CH.sub.2                                                                          CCH.sub.2                                                                               O OH      90-95                                             898 NH CH.sub.2                                                                          CCHCH.sub.3                                                                             O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                       899 NH CH.sub.2                                                                          CCHCH.sub.3                                                                             O OH                                                        900 NH CH.sub.2                                                                          CH(CH.sub.2 COOCH.sub.3)                                                                O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    Unmeasurable                                      901 NH CH.sub.2                                                                          CH(CH.sub.2 COOCH.sub.3)                                                                O OH                                                        __________________________________________________________________________

                  TABLE 54                                                         ______________________________________                                          ##STR457##                                                                    Com-                                                                           pound                                     m.p. (°C.)                    No.   a       b       d     e     R       or (n.sub.D.sup.20)                  ______________________________________                                         902   N       CH      CH    CH    H       159-161                              903   N       CH      CH    CH    OH      195-198                              904   N       CH      CH    CH    OCH.sub.3                                                                              160-162                              905   CH      N       CH    CH    H                                            906   CH      N       CH    CH    OH                                           907   CH      N       CH    CH    OCH.sub.3                                    908   CH      CH      N     CH    H                                            909   CH      CH      N     CH    OH                                           910   CH      CH      N     CH    OCH.sub.3                                    911   N       N       CH    CH    H                                            912   N       N       CH    CH    OH                                           913   N       N       CH    CH    OCH.sub.3                                    914   N       CH      N     CH    H                                            915   N       CH      N     CH    OH      174-177                              916   N       CH      N     CH    OCH.sub.3                                    917   N       CH      CH    N     H                                            918   N       CH      CH    N     OH      148-151                              919   N       CH      CH    N     OCH.sub.3                                                                              164-166                              920   CH      N       N     CH    H                                            921   CH      N       N     CH    OH                                           922   CH      N       N     CH    OCH.sub.3                                    923   CH      N       CH    N     H                                            924   CH      N       CH    N     OH                                           925   CH      N       CH    N     OCH.sub.3                                    926   CH      CH      N     N     H                                            927   CH      CH      N     N     OH                                           928   CH      CH      N     N     OCH.sub.3                                    ______________________________________                                    

                                      TABLE 55                                     __________________________________________________________________________      ##STR458##                                                                    Com-                                                                           pound                            m.p. (°C.)                             No. R.sup.1                                                                           R.sup.2      R        X   or (n.sub.D.sup.20)                           __________________________________________________________________________     929 CH.sub.3                                                                          COOCH(CH.sub.2 F).sub.2                                                                     OH       O   149-152                                       930 CH.sub.3                                                                          COOH         OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                    O   139-141                                       931 CH.sub.3                                                                          COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         OH       O   143.5-146                                     932 CH.sub.3                                                                          COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         OCH.sub.2 CHCH.sub.2                                                                    O   92-94                                         933 CH.sub.3                                                                          COOCH.sub.2 CH(OCH.sub.3).sub.2                                                             OH       O   153-155                                       934 CH.sub.3                                                                          COOCH.sub.2 CH(OCH.sub.3).sub.2                                                             OCH.sub.2 CHCH.sub.2                                                                    O   75-77                                         935 CH.sub.3                                                                          COOCH.sub.2 C(CH.sub.3)CH.sub.2                                                             OH       O   143-146                                       936 CH.sub.3                                                                          COOCH.sub.2 C(CH.sub.3)CH.sub.2                                                             OCH.sub.2 OCH.sub.3                                                                     O   98-100                                        937 CH.sub.3                                                                          COOC.sub.2 H.sub.4 N(CH.sub.3).sub.2                                                        OH       O   194-197                                       938 CH.sub.3                                                                          COOCH.sub.2 CHC(CH.sub.3).sub.2                                                             OCH.sub.2 OCH.sub.3                                                                     O   96-98                                         939 CH.sub.3                                                                          COOCH(CH.sub.3)CHCHCH.sub.3                                                                 OCH.sub.2 OCH.sub.3                                                                     O   72-75                                         940 CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 Cl                                                                  OCH.sub.2 CHCH.sub.2                                                                    O   114-116                                       941 CH.sub.3                                                                          COOCH(CH.sub.2 Cl).sub.2                                                                    OCH.sub.2 CHCH.sub.2                                                                    O   138-140                                       942 CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 F                                                                   OCH.sub.2 CHCH.sub.2                                                                    O   104-107                                       943 CH.sub.3                                                                          COOCH(CH.sub.3)CF.sub.3                                                                     OCH.sub.2 CHCH.sub.2                                                                    O   118-119.5                                     944 CH.sub.3                                                                          COOCH.sub.2 CHF.sub.2                                                                       OCH.sub.2 CHCH.sub.2                                                                    O   103-106                                       945 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 F                                                             OCH.sub.2 CHCH.sub.2                                                                    O   58-61                                         946 CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 OH                                                                     OCH.sub.2 CHCH.sub.2                                                                    O   121-124                                       947 CH.sub.3                                                                          COOCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                        OCH.sub.2 CHCH.sub.2                                                                    O   93-95                                         948 CH.sub.3                                                                           ##STR459##  OCH.sub.2 CHCH.sub.2                                                                    O   109-110                                       949 H  H            OH       N-Pym                                                                              190-193                                       950 H  H            OH       NH  169-170                                       951 CH.sub.3                                                                          CN                                                                                           ##STR460##                                                                             NH  169-172                                       __________________________________________________________________________      (In this Table, Pym indicates 4,6dimethoxypirimidin-2-yl.)               

                                      TABLE 56                                     __________________________________________________________________________     Com-                                                                           pound                           m.p. (°C.)                              No. R.sup.1                                                                           R.sup.2      R        X  or (n.sub.D.sup.20)                            __________________________________________________________________________     952 CH.sub.3                                                                          CN           OH       NH 185-189                                        953 CH.sub.3                                                                          CH.sub.2 CN                                                                                  ##STR461##                                                                             NH 151-156                                        954 CH.sub.3                                                                          COCOOC.sub.2 H.sub.5                                                                         ##STR462##                                                                             NH 150-153                                        955 CH.sub.3                                                                          COCOOC.sub.2 H.sub.5                                                                        OH       NH 179-183                                        956 CH.sub.3                                                                           ##STR463##                                                                                  ##STR464##                                                                             NH 82-85                                          957 CH.sub.3                                                                           ##STR465##  OH       NH 143-146                                        958 CH.sub.3                                                                           ##STR466##                                                                                  ##STR467##                                                                             NH 89-92                                          959 CH.sub.3                                                                           ##STR468##  OH       NH 127-129                                        960 CH.sub.3                                                                           ##STR469##                                                                                  ##STR470##                                                                             NH 94-99                                          961 CH.sub.3                                                                           ##STR471##  OH       NH 137-140                                        962 CH.sub.3                                                                           ##STR472##                                                                                  ##STR473##                                                                             NH 103-105                                        963 CH.sub.3                                                                           ##STR474##  OH       NH 170-173                                        964 CH.sub.3                                                                           ##STR475##                                                                                  ##STR476##                                                                             NH 106-109                                        965 CH.sub.3                                                                           ##STR477##  OH       NH 123-125                                        966 CH.sub.3                                                                           ##STR478##                                                                                  ##STR479##                                                                             NH 89-91                                          967 CH.sub.3                                                                           ##STR480##  OH       NH 140-143                                        __________________________________________________________________________

                                      TABLE 57                                     __________________________________________________________________________     Com-                                                                           pound                                m.p. (°C.)                         No. R.sup.1                                                                           R.sup.2         R          X  or (n.sub.D.sup.20)                       __________________________________________________________________________     968 CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                         OH         NH                                           969 CH.sub.3                                                                          COOCH2C CH      OH         NH                                           970 CH.sub.3                                                                          CONHCH.sub.3                                                                                    ##STR481##                                                                               NH                                           971 CH.sub.3                                                                          CONHCH.sub.3    OH         NH                                           972 CH.sub.3                                                                           ##STR482##                                                                                     ##STR483##                                                                               NH                                           973 CH.sub.3                                                                           ##STR484##     OH         NH                                           974 CH.sub.3                                                                           ##STR485##                                                                                     ##STR486##                                                                               NH                                           975 CH.sub.3                                                                           ##STR487##     OH         NH                                           976 CH.sub.3                                                                          COSCH.sub.3     OH         NH                                           977 CH.sub.3                                                                          COSC.sub.2 H.sub.5                                                                             OH         NH                                           978 CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                             OH         NH                                           979 CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                             OH         NH                                           980 CH.sub.3                                                                           ##STR488##     OH         NH                                           981 CH.sub.3                                                                           ##STR489##     OH         NH 172-176                                   982 CH.sub.3                                                                          CH.sub.3                                                                                        ##STR490##                                                                               NH 115-118                                   983 CH.sub.3                                                                          CH.sub.3        OH         NH 168-172                                   984 CH.sub.3                                                                          H               OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                        NH 52-55                                     985 CH.sub.3                                                                          COOH            OH         NH 178-182                                   986 CH.sub.3                                                                          COOCH.sub.2 OCH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                                                       NH 145-148                                   987 CH.sub.3                                                                           ##STR491##     OH         NH 203-206                                   __________________________________________________________________________

                  TABLE 58                                                         ______________________________________                                         Com-                                                                           pound                                   m.p. (°C.)                      No.   R.sup.1  R.sup.2   R         X    or (n.sub.D.sup.20)                    ______________________________________                                          988  CH.sub.3 COOC.sub.3 H.sub.7                                                                       OCH.sub.2 CHCH.sub.2                                                                     S                                            989  CH.sub.3 COOC.sub.3 H.sub.7                                                                       OH        S                                            990  CH.sub.3 COOC.sub.3 H.sub.7 -i                                                                    OH        S                                            991  CH.sub.3 COOC.sub.4 H.sub.9                                                                       OH        S                                            992  CH.sub.3 CONHC.sub.3 H.sub.7                                                                      OH        S                                            993  CH.sub.3 COSC.sub.2 H.sub.5                                                                       OH        S                                            994  H        COOC.sub.2 H.sub.5                                                                       OH        NH                                           995  Cl       COOC.sub.2 H.sub.5                                                                       OH        NH                                           996  CN       COOC.sub.2 H.sub.5                                                                       OH        NH                                           997  NO.sub.2 COOC.sub.2 H.sub.5                                                                       OH        NH                                           998  CH.sub.2 Cl                                                                             COOC.sub.2 H.sub.5                                                                       OH        NH                                           999  CH.sub.2 OH                                                                             COOC.sub.2 H.sub.5                                                                       OH        NH                                          1000  CH.sub.2 OCH.sub.3                                                                      COOC.sub.2 H.sub.5                                                                       OH        NH                                          1001  H        COCH.sub.3                                                                               OH        NH                                          1002  H        CHO       OH        NH                                          1003  H        CN        OH        NH                                          1004  H        CH.sub.3  OH        NH                                          1005  C.sub.2 H.sub.5                                                                         COOC.sub.2 H.sub.5                                                                       OH        NH                                          1006  C.sub.2 H.sub.5                                                                         H         OH        NH                                          ______________________________________                                    

                                      TABLE 59                                     __________________________________________________________________________      ##STR492##                                                                    Com-                                                                           pound                          m.p. (°C.)                               No. R.sup.1                                                                            R.sup.2    R       X   or (n.sub.D.sup.20)                             __________________________________________________________________________     1007                                                                               CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                     OCH.sub.2                                                                              O   120-121.5                                       1008                                                                               CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                     OCH.sub.2 CHCH.sub.2                                                                   O   1.5651                                          1009                                                                               CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                     OH      O   188-191                                         1010                                                                               CH.sub.3                                                                           COOCH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                                                                   O   118-122                                         1011                                                                               CH.sub.3                                                                            ##STR493##                                                                               OCH.sub.2 CHCH.sub.2                                                                   NH                                                  1012                                                                               CH.sub.3                                                                            ##STR494##                                                                               OH      NH                                                  1013                                                                               CH.sub.3                                                                           H          OH      NH                                                  __________________________________________________________________________

Compounds (I) of the present invention can be produced, for example, in accordance with the following processes 1 to 6. ##STR495## (wherein L¹ is a halogen atom, an alkylsulfonyl group, a benzylsulfonyl group or a substituted benzylsulfonyl group, and R, R³, R⁴, A, W, Y, Z and n are as defined above.)

A compound of the formula (I) can be produced by reacting a compound of the formula (II) with a compound of the formula (III) in a suitable solvent in the presence of an at least equal amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or acetonitrile, may, for example, be used.

The condensed heterocyclic carbonyl derivative (II) as the starting material can be obtained by known methods, for example, the methods disclosed in Bulletin de la Saciete Chimique de France), p. 2763-2766 (1975), J. Indian. Chem. Soc. Vol 45 (5), p. 439-445 (1968), Indian. J. Chem. Section B, 25B (8), p. 870-871 (1986), J. Chem. Soc. Organic Chemistry (1), p. 1-4 (1969), Indian. J. Chem. Section B, 15B (91), p. 1056-1058 (1977), Pract. Heterocyclic. Chem. Academic, p. 55 (1968), Organic Reaction, Vol 20, p. 337 (1973), Helvetica Chemica Acta., Vol 54, p. 959 (1970), J. Org. Chem., Vol 33 (12), p. 4426 (1968), Chemical and Pharmaceutical Bulletin, Vol 25 (11), p. 2988 (1977), and Parmaco, Edizione Scientifica (ITA), Vol 36 (9), p. 794 (1981).

Further, in a case where R in the formula (II) is H, a product wherein R is OH can be obtained by oxidation in accordance with a known method. ##STR496## (wherein R²¹ is an alkyl group, an allyl group, a benzyl group or a trimethylsilylethyl group, and A, W, Y, Z, R³, R⁴ and n are as defined above.)

When R²¹ is an alkyl group, a compound of the formula (V) can be produced by reacting a compound of the formula (IV) in water or in a suitable solvent containing water in the presence of an at least equimolar amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours, followed by acidifying.

As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, may be used.

As the solvent, an alcohol solvent such as methanol, ethanol or 2-propanol, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or diemthylsulfoxide, or other solvent such as acetonitrile, may, for example, be used.

When R²¹ is an allyl group, a product can be produced by reacting such a compound with dimedone or with an allyl acceptor such as formic acid or n-butylamine in a solvent such as acetonitrile, diemthylformamide or tetrahydrofuran using a palladium catalyst such as tetrakistriphenylphosphine palladium (O) at a temperature within a range of from room temperature to the boiling point of the solvent for from 1 to 24 hours.

Further, when R²¹ is a benzyl group, a product can be produced by hydrogenation in a suitable solvent using a platinum catalyst or palladium catalyst at an ordinary temperature under an ordinary pressure (if required, under heating and under pressure).

When R²¹ is a trimethylsilylethyl group, a product can be produced by reacting such a material with an at least equimolar amount of tetrabutylammonium fluoride or the like in tetrahydrofuran at room temperature.

As the solvent, an alcohol solvent such as methanol or ethanol, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such a.s acetone or methyl ethyl ketone, an ether solvent such as diethyl ether, 5 dioxane or tetrahydrofuran, or acetic acid, may, for example, be used. ##STR497## {wherein Q is a halogen atom, a cyano group, or an imidazolyl group, R²² is an alkoxy group which may be substituted, a benzyloxy group which may be substituted, an isopropylidenaminoxy group, a phenyloxy group which may be substituted, a phenylthio group which may be substituted, an alkenyloxy group, an alkynyloxy group, an alkylthio group, or a group of the formula --NR⁶ R⁷ (wherein each of R⁶ and R⁷ which may be the same or different, is a hydrogen atom, an alkyl group, a phenyl group which may be substituted, an alkylsulfonyl group, or a phenylsulfonyl group which may be substituted, or R⁶ and R⁷ may, together with the nitrogen atom, form a ring ), and R³, R⁴, A, W, Y, Z and n are as defined above.}

For the production of a compound of the formula (I) of the present invention, a compound of the formula (V) is reacted with an at least equimolar amount of a condensing agent in a suitable solvent at a temperature within a range of from -10° C. to the boiling point of the solvent for from 0.5 to 24 hours to obtain a compound of the formula (VI). After isolating or without isolating it, it is reacted with a compound of the formula (VII) together with an at least equimolar amount of a base in a suitable solvent at a temperature within a range of from -10° C. to the boiling point of the solvent for from 0.5 to 24 hours, to obtain a compound of the formula (I).

As the condensing agent, thionyl chloride, oxalic acid dichloride, a chlorocarbonic acid ester, carbonyl diimidazole, a cyanophospholic acid ester or a carbodiimide may, for example, be used.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR498## (wherein R³, R⁴, A, W, Y, Z and n are as defined above, and M is an alkali metal, an alkaline earth metal, ammonium or organic ammonium.)

A compound of the formula (VIII) can be produced by reacting the compound of the formula (V) together with an equimolar amount of a base in a suitable solvent at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal hydroxide or alkaline earth metal hydroxide such as sodium hydroxide or calcium hydroxide, an alkali metal carbonate or alkaline earth metal carbonate such as sodium carbonate or calcium carbonate, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as sodium methoxide or sodium ethoxide, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, ammonia, or an organic amine such as isopropylamine, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ester solvent such as methyl acetate or ethyl acetate, an alcohol solvent such as methanol, ethanol or 2-propanol, an ether solvent such as diethyl ether, tetrahydrofuran or dioxane, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile or water, may, for example, be used. ##STR499## (wherein A, R³, R⁴, W, Y, Z and n are as defined above.)

The compound of the formula (V) of the present invention can be obtained by reacting the compound of the formula (IX) with a suitable oxidizing agent in a suitable solvent at a temperature within a range of from 0° C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the oxidizing agent, a permanganate such as potassium permanganate, a chromic acid such as chromic anhydride, hydrogen peroxide, an organic peracid such as n-chloroperbenzoic acid, or nickel peroxide, may, for example, be used. As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile or water, may, for example, be used. ##STR500## (wherein R²³ is an alkyl group which may be substituted, a benzyl group which may be substituted, an alkenyl group, an alkynyl group, or a 2-trimethylsilylethoxymethyl group, L² is a hydrogen atom, and R³, R⁴, A, W, Y, Z and n are as defined above.)

A compound of the formula (XI) can be produced by reacting a compound of the formula (V) with a compound of the formula (X) in a suitable solvent in the presence of a base at a temperature within a range of from 10° C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, or an alkali metal hydride such as sodium hydride, may, for example, be used.

As the solvent, a ketone solvent such as acetone or methyl ethyl ketone, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR501## (wherein L³ is a leaving group such as a halogen, and R, R¹, R², R³, R⁴, R⁵, W and Z are as defined above, provided that R⁵ excludes a hydrogen atom.)

A compound of the formula (XIV) can be produced by reacting a compound of the formula (XII) with a compound of the formula (XIII) in a suitable solvent in the presence of an at least equimolar amount of a base at a temperature within a range of from -10° C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride such as sodium hydride or potassium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether or tetrahydrofuran, a ketone solvent such as acetone, an aprotic polar solvent such as N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR502## (wherein R²⁴ is a formyl group or a nitro group, and R¹, R³, R⁴, R, W, Y, Z and n are as defined above.)

A compound of the formula (XVI) can be obtained by subjecting the compound of the formula (XV) to a Vilsmeier reaction with phosphorus oxychloride in N,N-dimethylformamide to obtain a formyl product, or reacting it with a nitric acid ester in tetrahydrofuran in the presence of an alcoholate or reacting it with nitronium tetrafluoroborate in acetonitrile or in tetrahydrofuran at a temperature within a range of from -50° C. to the boiling point of the solvent, to obtain a nitro product.

Further, the obtained nitro product may be reduced by a conventional method to obtain an amino product, which can be led to various derivatives.

Among the compounds of the formula (I) of the present invention wherein A is (A-11), a compound of the formula (XIX) can be produced by the following process. ##STR503## (wherein X¹ and X² represent an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, R, R³, R⁴, R¹⁴, Q¹, W, Y, Z and n are as defined above, each of R²⁵ and R²⁶ which may be the same or different, is a chlorine atom, an alkoxy group or a lower alkylthio group.)

A compound of the formula (XIX) can be produced by reacting a compound of the formula (XVII) with a compound of the formula (XVIII) in a suitable solvent in the presence or absence of a base at a temperature within a range of from -30° C. to the boiling point of the solvent, preferably from 0° C. to 120° C., for from 0.5 to 24 hours.

As the base to be used, preferred is an organic base such as triethylamine, pyridine, N,N-diisopropylethylamine or N,N-dimethylaniline. However, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, may also be used.

As the solvent to be used, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be employed.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XII) can be produced by the following process. ##STR504## (wherein R⁵, R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X² represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, L⁴ is a chlorine atom or a bromine atom, and R, R³, R⁴, R¹⁴, W. Y, Z and n are as defined above.)

A compound of the formula (XXII) can be produced by reacting a compound of the formula (XX) with a compound of the formula (XXI) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 10° C. to 80° C., for from 1 to 20 hours.

As the base to be used, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal alkoxide such as potassium t-butoxide, or an organic base such as triethylamine, pyridine, N,N-diisopropylethylamine or N,N-dimethylaniline, may, for example, be employed.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylacetamide, N,N- dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used.

Among the compounds of the formula (I) wherein A is (A-12), a compound of the formula (XXVI) can be produced in accordance with the following process. ##STR505## (wherein R²⁷ is a group of the formula CR¹⁸ R¹⁹ (--CH═CHR¹⁸ or a group of the formula CR¹⁸ R¹⁹ C.tbd.CR¹⁸, R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X¹ represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, and L⁴, R, R³, R⁴, R¹⁴, W, Y, Z and n are as defined above.)

A compound of the formula (XXV) can be produced by reacting a compound of the formula (XXIII) with a compound of the formula (XXIV) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 1 to 24 hours.

As the base and the solvent to be used, the same as those described for Process 6 may be employed.

Further, a compound of the formula (XXVI) can be produced by subjecting a compound of the formula (XXV) to an intramolecular cyclization reaction in a suitable solvent in the presence of a suitable catalyst at a temperature of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 150° C., for from 5 to 72 hours.

As the catalyst to be used, an alkali metal carbonate such as potassium carbonate or sodium carbonate, or silver oxide (yellow), may, for example, be mentioned.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol, or an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide. However, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may also be used.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XXX) can be produced by the following process. ##STR506## (wherein R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X¹ represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, and L⁴, R, R³, R⁴, R¹⁴, W, Y, Z and n are as defined above.)

A compound of the formula (XXIX) can be produced by reacting a compound of the formula (XXVII) with a compound of the formula (XXVIII) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 3 to 24 hours. In this case, the reaction may be accelerated by an addition of an alkali metal iodide such as potassium iodide, as the case requires.

The base and the solvent to be used may be the same as those as described for Process 6.

Further, a compound of the formula (XXX) can be produced by subjecting a compound of the formula (XXIX) to hydrogenation in a suitable solvent in the presence of a palladium carbon catalyst at an ordinary temperature under an ordinary pressure for from 3 to 72 hours.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol. However, a hydrocarbon solvent such as benzene, toluene or xylene, an ether solvent such as tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may also be used.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XXXIV) can be produced by the following process. ##STR507## (wherein R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X¹ represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, and L⁴, R, R³, R⁴, R¹⁴, W, Y. Z and n are as defined above.)

A compound of the formula (XXXII) can be produced by reacting a compound of the formula (XXVII) with a compound of the formula (XXXI) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 5 to 24 hours. In this case, the reaction may be accelerated by an addition of an alkali metal iodide such as potassium iodide, as the case requires.

A compound of the formula (XXXIII) can be produced by subjecting a compound of the formula (XXXIV) to an intramolecular cyclization reaction in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 5 to 24 hours.

The base and the solvent to be used may be the same as those described for Process 6.

Further, a compound of the formula (XXXIV) can be produced by reducing a compound of the formula (XXXIII) in a suitable solvent using sodium hydrosulfite at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 30° C. to 50° C., for from 0.1 to 1 hour.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol, or water. However, an ether solvent such as tetrahydrofuran or 1,4-dioxane, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may be used in combination, as the case requires.

Now, the processes for the production of the compounds of the present invention, as well as methods for preparation of formulations and methods for application will be specifically described with reference to Examples.

BEST MODE FOR CARRYING OUT THE INVENTION EXAMPLE 1

Preparation of 5-(4, 6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene (Compound No. 104)

A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.

EXAMPLE 2

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methylbenzothiophene-4-carboxylic acid (Compound No. 105)

0.6 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene was dissolved in 80 ml of acetone. While stirring the solution at room temperature, 0.6 g of potassium permanganate dissolved in 10 ml of water was dropwise added thereto over a period of 15 minutes, and the mixture was further stirred at room temperature for 4 hours. It was then concentrated under reduced pressure to remove acetone, and then a saturated sodium bicarbonate aqueous solution was added thereto to make the mixture alkaline. The mixture was extracted with ethyl acetate, and then the aqueous layer was precipitated with 10% hydrochloric acid. The precipitated crystals were collected by filtration and washed with water to obtain 0.47 g (yield: 76%) of the desired compound.

EXAMPLE 3

Preparation of benzyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 1)

A mixture comprising 12.88 g of benzyl 3-ethoxycarbonyl-5-hydroxy-2-methylbenzofuran-5-carboxylate, 8.33 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 5.53 g of potassium carbonate in 150 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 14.45 g (yield: 81%) of the desired compound.

EXAMPLE 4

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic acid (Compound No. 2)

A mixture comprising 14.4 g of benzyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate and 4.52 g of 10% palladium carbon in 100 ml of ethanol, was subjected to hydrogenation under an ordinary pressure while stirring at room temperature. After completion of the reaction, an insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure, whereupon the precipitated crystals were washed with a solvent mixture of diethyl ether/n-hexane to obtain 10.47 g (yield: 89%) of the desired compound.

EXAMPLE 5

Preparation of pivaloyloxymethyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 4)

A mixture comprising 0.40 g of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 0.26 g of chloromethyl pivalate and 0.21 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was stirred at room temperature for 6 hours, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 0.43 g (yield: 84%) of the desired compound.

EXAMPLE 6

Preparation of methyl 5-(4,6-dimethoxypyrimidin-2-yl) oxybenzoxazol-4-carboxylate (Compound No. 446) A mixture comprising 0.6 g of methyl 5-hydroxybenzoxazol-4-carboxylate, 0.6 g of 2-chloro-4,6-dimethoxypyrimidine and 0.7 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 115° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =5/1) to obtain 0.4 g (yield: 39%) of the desired compound.

EXAMPLE 7

Preparation of methyl 6-(4, 6-dimethoxy-1,3,5-triazin-2-yl)oxybenzoxazol-7-carboxalate (Compound No. 464)

0.6 g of methyl 6-hydroxyybenzoxazol-7-carboxylate, 0.55 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 0.5 g of potassium carbonate in 30 ml of N,N-dimethylformamide were heated and stirred at 115° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 0.6 g (yield: 58%) of the desired compound.

EXAMPLE 8

Preparation of methyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate (Compound No. 507)

A mixture comprising 1.0 g of methyl 2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran-4-carboxylate, 1.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.78 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 100° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =4/1) to obtain 1.5 g (yield; 95%) of the desired compound.

EXAMPLE 9

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylic acid (Compound No. 508)

While stirring 1.2 g of methyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate in 20 ml of dimethylsulfoxide at room temperature, 2 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes and then the mixture was further stirred for 15 hours. The mixture was poured into water and extracted with diethyl ether. Then, the aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate, and the organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 1.0 g (yield: 87%) of the desired compound.

EXAMPLE 10

Preparation of sodium 3-benzoyl-5-(4, 6-dimethoxypyrimidin-2-yl) oxy-2-trifluoromethylbenzofuran-4-carboxylate (Compound No. 77)

While stirring 0.35 g of sodium hydride in 30 ml of N,N-dimethylformamide at room temperature, 1.73 g of 3-benzoyl-5-hydroxy-2-trifluoromethylbenzofuran-4-carboxylic acid was gradually added thereto. After completion of the addition, the mixture was further stirred for one hour. While stirring this mixture at room temperature, 1.08 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added thereto, and then the mixture was stirred at 70° C. for 3 hours. The mixture was returned to room temperature and poured into water. Precipitated crystals were separated by filtration and washed with water and acetone to obtain 1.02 g (yield: 40.5%) of the desired compound.

EXAMPLE 11

Preparation of benzyl 5-(4,6-dimethoxy-1,3, 5-triazin-2-yl)oxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate (Compound No. 32)

A mixture comprising 2 g of benzyl 5-hydroxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate, 1 g of 4,6-dimethoxy-2-methylsulfonyl-1,3,5-triazine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained solid was thoroughly washed with ethanol to obtain 2.4 g (yield: 86%) of the desired compound.

EXAMPLE 12

Preparation of methyl 6-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methyl-benzisoxazol-7-carboxylate (Compound No. 487)

A mixture comprising 1.3 g of methyl 6-hydroxy-3-methyl-benzisoxazol-7-carboxylate, 1.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained crystals were thoroughly washed with isopropyl ether to obtain 1.6 g (yield: 73%) of the desired compound.

EXAMPLE 13

Preparation of 6-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methyl-benzisoxazol-7-carboxylic acid (Compound No. 488)

While heating and stirring 1.0 g of methyl 6-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methylbenzisoxazol-7-carboxylate in 20 ml of N,N-dimethylsulfoxide at 70° C., 1.7 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes. Then, the mixture was further heated and stirred at 70° C. for 30 minutes. The mixture was returned to room temperature, then poured into water and extracted with diethyl ether. The aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was then concentrated under reduced pressure, and the crystals thereby obtained were washed with isopropyl ether to obtain 0.7 g (yield: 71%) of the desired compound.

EXAMPLE 14

Preparation of sodium 6-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 130)

While stirring 0.5 g of 5-(4, 6-dimethoxypyrimidin-2-yl) oxy-3-methoxycarbonyl-2-methyl-benzofuran-4-carboxylic acid in 5 ml of tetrahydrofuran at room temperature, 0.05 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 6 hours. Then, precipitated crystals were collected by filtration and washed with isopropyl ether to obtain 0.40 g (yield: 75%) of the desired compound.

EXAMPLE 15

Preparation of N- 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carbonyl!imidazole (Compound No. 16)

While stirring 0.8 g of 5-(4, 6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methyl-benzofuran-4-carboxylic acid in 30 ml of tetrahydrofuran at room temperature, 0.36 g of carbonyldiimidazole was added thereto. The mixture was stirred at room temperature for one hour and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water. It was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the crystals thereby obtained were washed with n-hexane to obtain 0.81 g (yield: 90%) of the desired compound.

EXAMPLE 16

Preparation of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carboxylic acid (Compound No. 371)

A mixture comprising 54.2 g of 4-allyloxycarbonyl-5-hydroxy-2-methylbenzofuran-3-carboxylic acid, 47 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 65 g of potassium carbonate in 200 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, and then the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Crystals obtained by concentration under reduced pressure, were washed with isopropyl ether to obtain 79.2 g (yield: 98%) of the desired compound.

EXAMPLE 17

Preparation of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-2-carbonyl chloride (Compound No. 254)

30.4 g of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl) oxy-2-methylbenzofuran-3-carboxylic acid was dissolved in 73 ml of thionyl chloride, and the solution was heated and stirred at 60° C. for 30 minutes. It was returned to room temperature, and then thionyl chloride was concentrated under reduced pressure. Toluene was added thereto, followed by further concentration. To the obtained oily substance, hexane was added for crystallization to obtain 31.4 g (yield: 99%) of the desired compound.

EXAMPLE 18

Preparation of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate (Compound No. 248)

3.0 g of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride was dissolved in 13 ml of dichloromethane, and 1.5 g of a 50% dimethylamine aqueous solution was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The oily substance obtained by concentration under reduced pressure, was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.84 g (yield; 60%) of the desired compound.

EXAMPLE 19

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylic acid (Compound No. 247)

1.40 g of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate and 0.29 g of formic acid were dissolved in 12 ml of tetrahydrofuran, and 37 mg of tetrakistriphenylphosphine palladium (0) was added thereto under a nitrogen atmosphere. The mixture was heated and stirred at 50° C. for 3 hours. The mixture was returned to room temperature, and then isopropyl ether was added to the reaction solution. Precipitated crystals were collected by filtration to obtain 1.02 g (yield: 80%) of the desired compound.

EXAMPLE 20

Preparation of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 152)

3.0 g of 4-allyloxycarobnyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride and 0.88 g of triethylamine were dissolved in 13 ml of dichloromethane, and 0.56 g of ethyl mercaptan was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =4/1) to obtain 1.74 g (yield: 55%) of the desired compound.

EXAMPLE 21

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylic acid (Compound No. 153)

1.60 g of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylate and 0.54 g of dimedone were dissolved in 14 ml of tetrahydrofuran, and 40 mg of tetrakistriphenylphosphine palladium (0) was added thereto under a nitrogen atmosphere. The mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to obtain 1.33 g (yield: 91%) of the desired compound.

EXAMPLE 22

Preparation of 2-trimethylsilylethoxymethyl 5-(4, 6-dimethoxypyrimidin-2-yl) oxy-3-(4-methoxybenzyloxycarbonyl)-2-methylbenzofuran-4-carboxylate (Compound No. 369) 13.5 g of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-(4-methoxybenzyloxycarbonyl)-2-methylbenzofuran-4-carboxylic acid and 3.3 g of triethylamine were dissolved in 120 ml of dichloromethane, and 5.0 g of 2-trimethylsilylethoxymethyl chloride was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =4/1) to obtain 14.0 g (yield: 82%) of the desired compound.

EXAMPLE 23

Preparation of methyl 6- (4, 6-dimethoxypyrimidin-2-yl)oxy!quinolin-5-carboxylate (Compound No. 904)

0.8 g of methyl 6-hydroxyquinolin-5-carboxylate, 0.96 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 0.82 g of potassium carbonate were stirred in 30 ml of N,N-dimethylformamide at 80° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from a solvent mixture of dichloromethane/isopropyl ether to obtain 1.21 g (yield: 89.0%) of the desired compound. mp: 160°-162° C.

EXAMPLE 24

Preparation of 6- (4, 6-dimethoxypyrimidin-2-yl)oxy!quinolin-5-carboxylic acid (Compound No. 903)

0.8 g of methyl 6- (4, 6-dimethoxypyrimidin-2-yl)oxy!quinolin-5-carboxylate was dissolved in 10 ml of methanol and 20 ml of methoxyethane, and 5 ml of an aqueous solution containing 0.39 g of potassium hydroxide was added thereto at 40° C. The mixture was extracted with dichloromethane. The aqueous layer was acidified (pH=4) with a 10% hydrochloric acid aqueous solution, and formed precipitates were collected by filtration and dried to obtain 0.5 g (yield: 66.0%) of the desired compound. mp: 195°-198° C.

EXAMPLE 25

Preparation of benzyl 5- (4, 6-dimethoxypyrimidin-2-yl) oxy!2-methylindol-4-carboxylate (Compound No. 664)

A mixture comprising 2.2 g of benzyl 5-hydroxy-2-methylindol-4-carboxylate, 1.7 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.3 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at a temperature of from 70° to 80° C. for two hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.8 g (yield: 85%) of the desired product. mp: 135°-139° C.

EXAMPLE 26

Preparation of benzyl 5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3-formyl-2-methylindol-4-carboxylate (Compound No. 680)

0.46 ml of phosphorus oxychloride was dropwise added to 1.8 ml of N,N-dimethylformamide under cooling with ice, and the mixture was stirred for 30 minutes. Then, 2.3 g of benzyl 5- (4,6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and the solution was dropwise added to the above mixture under cooling with ice. The mixture was stirred for 30 minutes, and then poured into ice water. An aqueous sodium hydroxide solution was added thereto for adjustment to pH9, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2 g (yield: 81.5%) of the desired compound. mp: 148°-149° C.

EXAMPLE 27

Preparation of allyl 5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-2-methyl-3-nitroindol-4-carboxylate (Compound No. 759)

2.0 g of allyl 5- (4, 6-dimethoxypyrimidin-2-yl)oxy!-2-methylindol-4-carboxylate was dissolved in 25 ml of acetonitrile, and the solution was cooled to -30° C. 16.3 ml of a 0.5M sulfolane solution of nitronium tetrafluoroborate was dropwise added thereto, and the mixture was stirred for 5 hours. After adding 2 ml of aqueous ammonia, the mixture was returned to room temperature and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Crystals obtained by concentration under reduced pressure, were washed with hexane to obtain 1.23 g (yield: 55%) of the desired compound.

EXAMPLE 28

Preparation of allyl 3-amino-5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylate (Compound No. 722)

3.4 g of allyl 5- (4,6-dimethoxypyrimidin-2-yl) oxy!-2-methyl-3-nitroindol-4-carboxylate was dissolved in 50 ml of methanol, and 5 ml of concentrated hydrochloric acid was added thereto. Then, 4.9 g of tin powder was gradually added at room temperature. Them, the mixture was stirred at room temperature for 12 hours. The solid was filtered off, and then residue was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.5 g (yield: 79%) of the desired product. mp: 132°-135° C.

EXAMPLE 29

Preparation of allyl 3-acetylamino-5- (4, 6-dimethoxypyrimidin-2-yl)oxy!-2-methylindol-4-carboxylate (Compound No. 735)

0.5 g of allyl 5- (4,6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylate was dissolved in 10 ml of pyridine, and 0.16 g of acetic anhydride was added thereto. The mixture was stirred for 12 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized with isopropyl ether to obtain 0.49 g (yield: 87%) of the desired compound. mp: 177°-180° C.

EXAMPLE 30

Preparation of 3-acetylamino-5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylic acid (Compound No. 736)

0.49 g of allyl 3-acetylamino-5- (4, 6-dimethoxypyrimidin-2-yl)oxy!-2-methylindol-4-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 0.1 g of dimedone and 0.01 g of tetrakistriphenylphosphine palladium were added thereto. The mixture was stirred at room temperature for 4 hours. Crystals obtained by concentration under reduced pressure, was washed with isopropyl ether to obtain 0.41 g (yield: 93%) of the desired compound. mp: 230°-233° C.

EXAMPLE 31

Preparation of benzyl-l-benzoyl-5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylate (Compound No. 796)

1.5 g of benzyl 5- (4,6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of tetrahydrofuran, and 0.176 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 30 minutes. Then, 0.51 g of benzoyl chloride was dropwise added thereto at room temperature, and the mixture was stirred for 4 hours. After concentration under reduced pressure, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 1.67 g (yield: 92%) of the desired compound. mp: 128°-132.5° C.

EXAMPLE 32

Preparation of l-benzoyl-5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylic acid (Compound No. 797)

1.6 g of benzyl 1-benzoyl-5- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of ethyl acetate, and 0.1 g of 10% palladium carbon was added thereto. Then, catalytic reduction was conducted. Insoluble matters were filtered off, and then filtrate was concentrated under reduced pressure. The residue thereby obtained was washed with isopropyl ether to obtain 1.28 g (yield: 97%) of the desired compound. mp: 113°-115° C.

EXAMPLE 33

Preparation of (2-trimethylsilyl)ethyl 6- (4, 6-dimethoxypyrimidin-2-yl) oxy!-2-oxobenzoxazolin-7-carboxylate (Compound No. 853)

1.18 g of triphosgene was gradually added at room temperature to a mixture comprising 2.45 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate and 5 ml of triethylamine in 20 ml of dichloromethane. The mixture was stirred at room temperature for one hour, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, 10% hydrochloric acid and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 2.25 g (yield: 97%) of the desired compound. (Yield: 86.5%) Refractive index: unmeasurable

EXAMPLE 34

Preparation of (2-trimethylsilyl)ethyl 7- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3-oxo-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 878)

0.60 g of chloroacetyl chloride was gradually dropwise added at 10° C. to a mixture comprising 2.04 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6- (4,6-dimethoxypyrimidin-2-yl) oxy!benzoate and 1.38 g of potassium carbonate in 15 ml of N,N-dimethylformamide, and then the mixture was gradually returned to room temperature and stirred for 5 hours. Further, the mixture was stirred at 50° C. for two hours to complete the reaction. The mixture was returned to room temperature, then poured into water, adjusted to pH3 with 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 1.01 g (yield: 41.8%) of the desired compound. mp: 148°-150° C.

EXAMPLE 35

Preparation of (2-trimethylsilyl)ethyl 7- (4, 6-dimethoxypyrimidin-2-vl) oxy!-2-methylene-3, 4-dihydro-2H-1,4-benzoxadin-8-carboxylate (Compound No. 896)

A mixture comprising 4.20 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6- (4, 6-dimethoxypyrimidin-2-yl) oxy!benzoate, 1.68 g of sodium carbonate and 1.42 g of propargyl bromide in 20 ml of N,N-dimethylformamide was heated and stirred at 50° C. for 4 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 2.90 g (yield: 63.9%) of (2-trimethylsilyl) ethyl 2-hydroxy-3-propargylamino-6- (4, 6-dimethoxypryrimidin-2-yl)oxy!benzoate.

A mixture comprising 2.80 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-propargylamino-6- (4, 6-imethoxypyrimidin-2-yl)oxy!benzoate thus obtained and 0.20 g of mercury oxide (yellow) in 10 ml of N,N-imethylfromamide was heated and stirred under a nitrogen stream at 150° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 1.80 g of the desired compound. Refractive index: unmeasurable

EXAMPLE 36

Preparation of (2-trimethylsilyl)ethyl 7- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3-methyl-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 890)

1.20 g of chloroacetone was gradually dropwise added at 10° C. to a mixture comprising 3.50 g of (2-trimethylsilyl) ethyl 2-hydroxy-3-nitro-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate, 1.80 g of potassium carbonate and 1.33 g of potassium iodide in 20 ml of acetone. Then, mixture was gradually returned to room temperature and stirred for 8 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure, poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 3.70 g (yield: 63.9%) of (2-trimethylsilyl)ethyl 2-acetonyloxy-3-nitro-6- (4,6-dimethoxypyrimidin-2-yl) oxy!benzoate (yield: 93.7%)

3.60 g of (2-trimethylsilyl) ethyl-2-acetonitrileoxy-3-nitro-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate thus obtained was subjected to catalytic reduction under an ordinary pressure in 100 ml of methanol by means of 0.5 g of 10% palladium carbon. The reaction was terminated when the theoretical amount of about 700 ml of hydrogen was consumed. Palladium carbon was filtered off, and the filtrate was concentrated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography to obtain 3.10 g (yield: 94.8%) of the desired compound. Refractive index: unmeasurable

EXAMPLE 37

Preparation of (2-trimethylsilyl)ethyl 7- (4, 6-dimethoxypyrimidin-2-yl) oxy!-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 884)

A mixture comprising 3.50 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-nitro-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate, 3.40 g of potassium carbonate and 9.40 g of 1,2-dibromoethane in 20 ml of N,N-dimethylformamide was heated and stirred at 80° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 3.60 g (yield: 82.8%) of (2-trimethylsilyl)ethyl 2-(2-bromoethoxy)-3-nitro-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate. 3.60 g of (2-trimethylsilyl)ethyl 2-(2-bromoethoxy-3-nitro-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate thus obtained and 7.00 g of 70% sodium hydrosulfite in a solvent mixture of water (15 ml) and methanol (30 ml) were stirred at room temperature for 20 minutes. The mixture was poured into water, saturated with sodium chloride and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and then extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. 3.10 g of (2-trimethylsilyl)ethyl 3-amino-2-(2-bromoethoxy)-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate was obtained by concentration under reduced pressure. This product was used for the next reaction without purification. (Yield: 91.2%)

3.10 g of (2-trimethylsilyl)ethyl 3-amino-2-(2-bromoethoxy)-6- (4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate and 2.76 g of potassium carbonate in 10 ml of N,N-dimethylformamide were stirred at a temperature of from 60° C. to 80° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. 1.95 g (yield: 75.0%) of the desired compound was obtained by concentration under reduced pressure. Refractive index: 1.5333

EXAMPLE 38

Preparation of 7- (4,6-dimethoxypyrimidin-2-yl) oxy!-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylic acid (Compound No. 885)

15 ml of 1M tetrahydrofuran solution of tetrabutylammonium fluoride trihydrate was added to 1.65 g of (2-trimethylsilyl)ethyl 7- (4,6-dimethoxypyrimidin-2-yl) oxy!-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylate obtained in Example 39 in 30 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated under reduced pressure, poured into water, adjusted to pH5 with a 20% citric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 0.87 g (yield: 68.5%) of the desired compound. mp: 160°-164° C.

The herbicide of the present invention comprises a condensed heterocyclic derivative of the formula (I) as an active ingredient.

For the compound of the present invention to be used as a herbicide, the compound of the present invention may be used by itself. However, it may be used in the form of a formulation such as a dust, a wettable powder, an emulsifiable concentrate, a microgranule or a granule by blending it with a carrier which is commonly used for formulations, a surfactant, a dispersant or an adjuvant.

The carrier to be used for such formulations, may, for example, be a solid carrier such as Jeaklite, talc, bentonite, clay, kaolin, diatomaceous earth, fine silica, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexane or methylnaphthalene.

As the surfactant and dispersant, a metal salt of alkylbenzenesulfonic acid, a metal salt of dinaphthylmethane disulfonic acid, a salt of alcohol sulfuric acid ester, an alkylaryl sulfonate, a lignin sulfonate, a polyoxyethylene glycol ether, a polyoxyethylene alkylaryl ether or a polyoxyethylene sorbitol monoalkylate may, for example, be mentioned.

The adjuvant may, for example, be carboxymethyl cellulose, polyethylene glycol or gum arabic.

In practical use, the herbicide may be diluted to a suitable concentration before application, or may be directly applied.

The herbicide of the present invention may be used for application to foliage, soil or water surface. The blending proportion of the active ingredient is suitably selected as the case requires. However, in a case of a dust or a granule, the proportion of the active ingredient is selected suitably within a range of from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight. In a case of an emulsifiable concentrate or a wettable powder, the proportion is selected suitably within a range of from 1 to 50% by weight, preferably from 5 to 20% by weight.

The dose of the herbicide of the present invention varies depending upon the type of the compound, the weeds to be controlled, the germination tendency, the environmental conditions and the type of the formulation to be used. However, in the case of a dust or a granule which is used by itself, the dose of the active ingredient is selected suitably within a range of from 0.1 g to 5 kg, preferably from 1 g to 1 kg, per 10 ares. In a case of an emulsifiable concentrate or a wettable powder which is used in a liquid state, the dose of the active ingredient is selected suitably within a range of from 1 to 50,000 ppm, preferably from 10 to 10,000 ppm.

Further, the compound of the present invention may be used in combination with an insecticide, a fungicide, other herbicide, a plant growth controlling agent, a fertilizer or the like, as the case requires.

Now, the formulation method will be described with reference to typical Formulation Examples. The compounds, types of the additives and blending ratios are not limited to such specific Examples and may be changed within wide ranges. In the following description, "parts" means "parts by weight".

FORMULATION EXAMPLE 1 (Wettable powder)

To 10 parts by weight of Compound No. 172, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth and 69 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2 (Wettable powder)

To 10 parts of Compound No. 2, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 3 (Wettable powder)

To 10 parts of Compound No. 24, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of calcium carbonate, were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 4 (Emulsifiable concentrate)

To 10 parts of Compound No. 9, 80 parts of a mixture comprising equal amounts of xylene and isophorone and 10 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate, were added, and the mixture was thoroughly stirred to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 5 (Granule)

1 part of Compound No. 168, 89 parts of a bulking agent comprising a 1:3 mixture of talc and bentonite, 5 parts of fine silica, 5 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate and 10 parts of water were mixed and thoroughly kneaded to obtain a paste, which was extruded from sieve apertures with a diameter of 0.7 mm. The extruded product was dried and then cut into a length of from 0.5 to 1 mm to obtain granules.

Now, the herbicidal effects of the compounds of the present invention will be described with reference to Test Examples.

TEST EXAMPLE 1 (Test on herbicidal effects by paddy field soil treatment)

In a plastic pot (surface area: 100 cm²) filled with paddy field soil, barnyardgrass (Eo), monochoria (Mo) and bulrush (Sc) were sown after puddling and leveling, and flooded to a water depth of 3 cm. Next day, a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The dose was 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 62-65.

                  TABLE 60                                                         ______________________________________                                                       Herbicidal effects                                               Index         (growth-controlling degree)                                      No.           or phytotoxicity                                                 ______________________________________                                         5             Herbicidal effect or phytotoxicity:                                            at least 90%                                                     4             Herbicidal effect or phytotoxicity:                                            at least 70% and less than 90%                                   3             Herbicidal effect or phytotoxicity:                                            at least 50% and less than 70%                                   2             Herbicidal effect or phytotoxicity:                                            at least 30% and less than 50%                                   1             Herbicidal effect or phytotoxicity:                                            at least 10 and less than 30%                                    0             Herbicidal effect or phytotoxicity:                                            0 to less than 10%                                               ______________________________________                                    

                  TABLE 61                                                         ______________________________________                                         Structural formulae    References                                              ______________________________________                                         Comparative compound A                                                          ##STR508##            Japanese Unexamined Patent Publication No.                                     121973/1990 Japanese Unexamined Patent Publication                             No. 56469/1990                                          Comparative compound B                                                          ##STR509##            Japanese Unexamined Patent Publication No.                                     121973/1990 Japanese Unexamined Patent Publication                             No. 56469/1990                                          Comparative compound C                                                          ##STR510##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             Comparative compound D                                                          ##STR511##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             Comparative compound E                                                          ##STR512##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             Comparative compound F                                                          ##STR513##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             ______________________________________                                    

                  TABLE 62                                                         ______________________________________                                         Compound   Herbicidal effect                                                   No.        Eo            Mo    Sc                                              ______________________________________                                          1         5             5     5                                                2         5             5     5                                                4         5             5     5                                                8         5             5     5                                                9         5             5     5                                               10         5             5     5                                               11         5             5     5                                               12         5             5     5                                               13         5             5     5                                               16         5             5     5                                               24         5             5     5                                               26         5             5     5                                               34         5             5     5                                               35         5             5     5                                               36         5             5     5                                               38         5             5     5                                               40         5             5     5                                               42         5             5     5                                               45         5             5     5                                               48         5             5     5                                               50         5             5     5                                               59         5             5     5                                               61         5             5     5                                               62         5             5     5                                               63         5             5     5                                               71         5             5     5                                               88         5             5     5                                               105        5             5     5                                               165        5             5     5                                               167        5             5     5                                               169        5             5     5                                               171        5             5     5                                               172        5             5     5                                               178        5             5     5                                               ______________________________________                                    

                  TABLE 63                                                         ______________________________________                                         Compound   Herbicidal effect                                                   No.        Eo            Mo    Sc                                              ______________________________________                                         182        5             5     5                                               262        5             5     5                                               286        5             5     5                                               301        5             5     5                                               365        5             5     5                                               405        5             5     5                                               445        5             5     5                                               505        5             5     5                                               506        5             5     5                                               507        5             5     5                                               508        5             5     5                                               509        5             5     5                                               511        5             5     5                                               512        5             5     5                                               515        5             5     4                                               516        5             5     4                                               519        5             5     5                                               520        5             5     5                                               522        5             5     5                                               523        5             5     5                                               524        5             5     5                                               525        5             5     5                                               526        5             5     5                                               527        5             5     5                                               528        5             5     5                                               529        5             5     5                                               530        5             5     5                                               531        5             5     5                                               533        5             5     5                                               535        5             5     5                                               539        5             5     5                                               541        5             5     5                                               542        5             5     5                                               543        5             5     5                                               ______________________________________                                    

                  TABLE 64                                                         ______________________________________                                         Compound   Herbicidal effect                                                   No.        Eo            Mo    Sc                                              ______________________________________                                         534        5             5     5                                               544        5             5     5                                               545        5             5     5                                               546        5             5     5                                               547        5             5     5                                               548        5             5     5                                               549        5             5     5                                               550        5             5     5                                               551        5             5     5                                               553        5             5     5                                               554        5             5     5                                               555        5             5     5                                               556        5             5     5                                               558        5             5     5                                               562        5             5     5                                               563        5             5     5                                               564        5             5     5                                               567        5             5     5                                               568        5             5     5                                               572        5             5     5                                               573        5             5     5                                               575        5             5     5                                               578        5             5     5                                               584        5             5     5                                               588        5             5     5                                               589        5             5     5                                               591        5             5     5                                               593        5             5     5                                               594        5             5     5                                               595        5             5     5                                               596        5             5     5                                               597        5             5     5                                               598        5             5     5                                               599        5             5     5                                               ______________________________________                                    

                  TABLE 65                                                         ______________________________________                                         Compound   Herbicidal effect                                                   No.        Eo            Mo    Sc                                              ______________________________________                                         600        5             5     5                                               611        5             5     5                                               613        5             5     5                                               614        5             5     5                                               615        5             5     5                                               616        5             5     5                                               619        5             5     5                                               622        5             5     5                                               626        5             5     5                                               628        5             5     4                                               665        5             5     5                                               671        5             5     5                                               681        5             5     5                                               693        5             5     5                                               770        3             5     5                                               772        5             5     5                                               787        5             5     5                                               789        5             5     5                                               797        5             5     5                                               813        5             5     5                                               815        5             5     5                                               831        5             5     5                                               834        5             3     5                                               929        5             5     5                                               931        5             5     5                                               933        5             5     5                                               952        5             5     5                                               955        5             5     5                                               Comparative                                                                               0             0     0                                               compound A                                                                     Comparative                                                                               4             1     2                                               compound B                                                                     Comparative                                                                               0             0     0                                               compound E                                                                     Comparative                                                                               0             0     0                                               compound F                                                                     ______________________________________                                    

TEST EXAMPLE 2 (Test on herbicidal effects by upland field soil treatment)

In a plastic pot.(surface area: 120 cm²) filled with upland field soil, barnyardgrass (Ec), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 66-69.

                  TABLE 66                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                          2        5         5     5        5   5                                        4        5         5     5        5   5                                        8        5         5     5        5   5                                        9        5         5     5        5   5                                       10        5         5     5        5   5                                       11        5         5     5        5   5                                       12        5         5     5        5   5                                       13        5         5     5        5   5                                       16        5         5     5        5   5                                       24        5         5     5        5   5                                       26        5         5     5        5   5                                       30        5         5     5        5   5                                       34        5         5     5        5   5                                       35        5         5     5        5   5                                       36        5         5     5        5   5                                       38        5         5     5        5   5                                       40        5         5     5        5   5                                       42        5         5     5        5   5                                       48        5         5     5        5   5                                       50        5         5     5        5   5                                       59        5         5     5        5   5                                       61        5         5     5        5   5                                       62        5         5     5        5   5                                       88        5         5     5        5   5                                       105       5         5     5        5   5                                       109       5         5     5        5   5                                       165       5         5     5        5   5                                       167       5         5     5        5   5                                       169       5         5     5        5   5                                       171       5         5     5        5   5                                       172       5         5     5        5   5                                       178       5         5     5        5   5                                       204       5         5     5        5   5                                       262       5         4     5        5   5                                       ______________________________________                                    

                  TABLE 67                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         286       5         5     5        5   5                                       301       4         5     5        5   5                                       386       5         5     5        5   5                                       506       5         5     5        5   5                                       507       4         5     5        5   5                                       508       5         5     5        5   5                                       509       4         5     5        5   4                                       511       5         5     5        5   5                                       512       5         5     5        5   5                                       519       5         5     5        5   5                                       520       5         5     5        5   5                                       522       5         5     5        5   5                                       523       5         5     5        5   5                                       524       5         5     5        5   5                                       525       5         5     5        5   5                                       526       5         5     5        5   5                                       528       5         5     5        5   5                                       529       5         5     5        5   5                                       530       5         5     5        5   5                                       531       5         5     5        5   5                                       533       5         5     5        5   5                                       537       4         5     5        5   5                                       539       5         5     5        5   5                                       541       5         5     5        5   5                                       543       5         5     5        5   5                                       544       5         5     5        5   5                                       546       5         5     5        5   5                                       547       5         5     5        5   5                                       548       5         5     5        5   5                                       549       5         5     5        5   5                                       550       5         5     5        5   5                                       551       5         5     5        5   5                                       553       5         5     5        5   5                                       554       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 68                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         555       5         5     5        5   5                                       556       4         5     5        5   5                                       558       4         5     5        5   5                                       562       5         5     5        5   5                                       563       5         5     5        5   5                                       564       4         5     5        5   5                                       567       4         5     5        5   5                                       568       5         5     5        5   5                                       573       5         5     5        5   5                                       575       5         5     5        5   5                                       578       5         5     5        5   5                                       584       5         5     5        5   5                                       588       5         5     5        5   5                                       589       5         5     5        5   5                                       591       5         5     5        5   5                                       594       5         5     5        5   5                                       595       5         5     5        5   5                                       596       5         5     5        5   5                                       597       5         5     5        5   5                                       598       5         5     5        5   5                                       599       5         5     5        5   5                                       600       4         5     5        5   5                                       611       5         5     5        5   5                                       613       5         5     5        5   5                                       614       5         5     5        5   5                                       615       4         5     5        5   5                                       616       5         5     5        5   5                                       626       5         5     5        5   5                                       627       4         5     5        5   5                                       628       5         5     5        5   5                                       665       5         5     5        5   5                                       667       3         5     5        5   5                                       681       5         5     5        5   5                                       693       3         5     5        5   5                                       ______________________________________                                    

                  TABLE 69                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         770       3         5     5        5   5                                       772       5         5     5        5   5                                       787       5         5     5        5   5                                       789       5         5     5        5   5                                       797       3         5     5        5   5                                       815       5         5     5        5   5                                       831       3         5     5        5   5                                       834       3         5     5        5   5                                       852       2         5     5        5   5                                       883       3         5     5        3   5                                       929       4         5     4        4   5                                       931       5         5     5        4   5                                       933       5         5     5        5   5                                       952       5         4     5        5   5                                       984       4         5     5        5   5                                       Comparative                                                                              0         0     0        0   0                                       compound A                                                                     Comparative                                                                              0         0     2        3   0                                       compound B                                                                     Comparative                                                                              1         2     5        4   2                                       compound C                                                                     Comparative                                                                              0         2     4        4   1                                       compound D                                                                     Comparative                                                                              0         0     2        0   1                                       compound E                                                                     Comparative                                                                              0         0     0        0   0                                       compound F                                                                     ______________________________________                                    

TEST EXAMPLE 3 (Test on herbicidal effects by upland field foliage treatment)

In a plastic pot (surface area: 120 cm²) filled with upland field soil, barnyardgrass (Ec), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil and were cultured in a green house for 2 weeks. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in the green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 70-74.

                  TABLE 70                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                          1        5         5     5        5   5                                        2        5         5     5        5   5                                        4        5         5     5        5   5                                        8        5         5     5        5   5                                        9        5         5     5        5   5                                       10        5         5     5        5   5                                       11        5         5     5        5   5                                       12        5         5     5        5   5                                       13        5         5     5        5   5                                       16        5         5     5        5   5                                       24        5         5     5        5   5                                       26        5         5     5        5   5                                       30        5         5     5        5   5                                       34        5         5     5        5   5                                       35        5         5     5        5   5                                       36        5         5     5        5   5                                       38        5         5     5        5   5                                       40        5         5     5        5   5                                       42        5         5     5        5   5                                       48        5         5     5        5   5                                       59        5         5     5        5   5                                       61        5         5     5        5   5                                       62        5         5     5        5   5                                       71        5         5     5        5   5                                       88        5         5     5        5   5                                       105       5         5     5        5   5                                       159       3         5     5        4   5                                       162       5         5     5        5   5                                       165       5         5     5        5   5                                       167       5         5     5        5   5                                       169       5         5     5        5   5                                       171       5         5     5        5   5                                       178       5         5     5        5   5                                       204       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 71                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         262       5         5     5        5   5                                       286       5         5     5        5   5                                       301       5         5     5        5   3                                       344       3         5     5        5   4                                       365       3         5     5        5   5                                       367       4         5     5        4   5                                       445       5         5     5        5   5                                       488       5         5     5        5   5                                       505       5         5     5        5   4                                       506       5         5     5        5   5                                       507       5         5     5        5   5                                       508       5         5     5        5   5                                       509       5         5     5        5   5                                       511       5         5     5        5   5                                       512       5         5     5        5   5                                       519       5         5     5        5   5                                       520       5         5     5        5   5                                       523       5         5     5        5   5                                       524       5         5     5        5   5                                       525       3         5     5        5   3                                       526       5         5     5        5   5                                       528       5         5     5        5   5                                       529       5         5     5        5   5                                       530       5         5     5        5   5                                       531       5         5     5        5   5                                       533       5         5     5        5   5                                       534       4         5     5        4   5                                       539       5         5     5        5   5                                       540       3         5     5        5   3                                       541       5         5     5        5   5                                       543       5         5     5        5   5                                       544       5         5     5        5   5                                       546       5         5     5        5   5                                       547       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 72                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         548       5         5     5        5   5                                       549       5         5     5        5   5                                       550       5         5     5        5   5                                       551       5         5     5        5   5                                       553       5         5     5        5   5                                       554       5         5     5        4   5                                       555       5         5     5        3   5                                       556       4         5     5        4   5                                       558       5         5     5        5   5                                       562       5         5     5        5   5                                       563       5         5     5        5   5                                       564       5         5     5        5   5                                       567       5         5     5        5   5                                       568       5         5     5        5   5                                       573       5         5     5        5   5                                       575       5         5     5        5   5                                       578       5         5     5        5   5                                       584       5         5     5        5   5                                       588       5         5     5        5   5                                       589       5         5     5        5   5                                       591       5         5     5        5   5                                       594       5         5     5        5   5                                       595       5         5     5        5   5                                       596       5         5     5        5   5                                       597       5         5     5        5   5                                       598       5         5     5        5   5                                       599       5         5     5        5   5                                       600       5         5     5        5   5                                       611       5         5     5        5   5                                       613       5         5     5        5   5                                       614       5         5     5        5   5                                       615       5         5     5        5   5                                       616       5         5     5        5   5                                       619       4         5     5        5   5                                       ______________________________________                                    

                  TABLE 73                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         622       4         5     5        5   4                                       627       5         5     5        5   5                                       628       5         5     5        5   4                                       665       5         5     5        5   5                                       667       5         5     5        5   5                                       671       5         5     5        5   5                                       681       5         5     5        5   3                                       691       5         5     5        5   5                                       693       5         5     5        5   5                                       714       5         5     5        5   5                                       738       5         3     5        4   5                                       740       5         5     5        5   5                                       760       3         5     5        4   5                                       770       5         5     5        5   5                                       772       5         5     5        5   5                                       787       5         5     5        5   5                                       789       5         5     5        5   5                                       797       5         5     5        5   5                                       813       5         5     5        5   5                                       815       5         5     5        5   5                                       827       4         5     5        5   3                                       829       5         5     5        5   4                                       831       5         5     5        5   5                                       852       3         5     5        4   3                                       854       5         5     5        3   4                                       885       5         5     5        5   5                                       887       4         5     5        5   5                                       891       5         5     5        5   5                                       892       5         5     5        5   5                                       897       5         5     5        3   5                                       929       5         5     5        5   5                                       931       5         5     5        5   5                                       933       5         5     5        5   5                                       952       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 74                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         955       5         5     5        5   5                                       683       5         5     5        5   5                                       984       5         5     5        5   5                                       958       5         5     5        5   5                                       Comparative                                                                              0         0     0        0   0                                       compound A                                                                     Comparative                                                                              0         2     3        3   0                                       compound B                                                                     Comparative                                                                              2         1     4        5   2                                       compound C                                                                     Comparative                                                                              0         1     2        4   0                                       compound D                                                                     Comparative                                                                              0         4     3        0   1                                       compound E                                                                     Comparative                                                                              0         0     0        0   0                                       compound F                                                                     ______________________________________                                    

TEST EXAMPLE 4 (Test on crop plant selectivity by paddy field soil treatment)

In a 1/10,000a plastic pot, paddy field soil was filled, irrigated, paddled and leveled. Then, barnyardgrass (Eo), monochoria (Mo) and bulrush (Sc) were sown at a depth of 0.5 cm. Further, two seedlings of rice (Or) of 2.5 leaf stage was transplanted at a transplantation depth of 2 cm. Then, the pot was flooded to a water depth of 3 cm. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 28th day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 75 to 77.

                  TABLE 75                                                         ______________________________________                                                              Herbicidal   Phyto-                                       Compound  Dose       effect       toxicity                                     No.       (g.sup.ai /10a)                                                                           Eo    Mo     Sc  Or                                       ______________________________________                                          1        25         4     4      3   0                                         2        1.6        5     5      4   0                                         4        6.3        5     5      3   1                                         8        6.3        5     5      5   0                                         9        6.3        5     5      5   0                                         10       6.3        5     5      5   0                                         11       6.3        5     5      5   1                                         12       1.6        5     5      3   0                                         34       6.3        5     5      5   0                                         35       6.3        5     5      5   1                                         36       1.6        5     5      3   0                                         59       25         5     5      3   0                                        105       25         5     5      3   0                                        165       6.3        5     5      5   0                                        167       25         5     5      5   0                                        169       25         5     5      5   0                                        171       6.3        5     5      5   0                                        172       6.3        5     5      5   0                                        178       25         4     5      5   0                                        262       6.3        4     5      3   0                                        504       25         5     5      3   0                                        509       6.3        5     5      5   0                                        511       1.6        5     5      4   0                                        522       6.3        5     5      5   0                                        523       25         5     5      5   1                                        524       25         5     5      5   0                                        525       6.3        5     5      5   0                                        526       1.6        5     5      4   0                                        528       1.6        5     5      5   0                                        529       1.6        5     5      5   0                                        530       6.3        5     5      5   0                                        531       1.6        5     5      4   1                                        533       6.3        5     5      5   0                                        ______________________________________                                    

                  TABLE 76                                                         ______________________________________                                                              Herbicidal   Phyto-                                       Compound  Dose       effect       toxicity                                     No.       (g.sup.ai /10a)                                                                           Eo    Mo     Sc  Or                                       ______________________________________                                         534       6.3        5     5      5   0                                        541       6.3        5     5      3   0                                        543       6.3        5     5      3   0                                        544       6.3        5     5      5   0                                        545       6.3        3     5      3   0                                        546       6.3        5     5      3   0                                        547       6.3        4     5      4   0                                        548       6.3        4     4      3   0                                        549       6.3        5     5      4   0                                        550       6.3        5     5      3   0                                        551       6.3        5     5      5   0                                        553       6.3        5     5      5   1                                        554       6.3        5     5      5   0                                        555       25         5     5      5   0                                        556       25         5     5      5   0                                        562       6.3        5     5      5   1                                        563       25         5     5      5   0                                        568       25         3     5      5   0                                        572       25         4     5      4   0                                        573       25         5     5      5   0                                        578       25         5     5      5   1                                        600       25         4     5      3   1                                        611       6.3        5     5      3   1                                        613       6.3        5     5      4   0                                        614       6.3        4     5      3   0                                        616       6.3        5     5      5   0                                        623       6.3        4     5      5   0                                        681       25         5     5      4   1                                        797       6.3        4     5      3   0                                        831       6.3        5     5      5   0                                        929       6.3        5     5      5   0                                        931       25         5     5      5   0                                        933       25         4     5      5   1                                        ______________________________________                                    

                  TABLE 77                                                         ______________________________________                                                              Herbicidal   Phyto-                                       Compound  Dose       effect       toxicity                                     No.       (g.sup.ai /10a)                                                                           Eo    Mo     Sc  Or                                       ______________________________________                                         955       25         4     5      5   1                                        Comparative                                                                              25         0     0      0   0                                        compound A                                                                     Comparative                                                                              25         2     0      0   0                                        compound B                                                                     Comparative                                                                              25         3     4      3   4                                        compound C                                                                     Comparative                                                                              25         2     3      1   3                                        compound D                                                                     Comparative                                                                              100        0     0      0   0                                        compound E                                                                     Comparative                                                                              100        0     0      0   0                                        compound F                                                                     ______________________________________                                    

TEST EXAMPLE 5 (Test on crop plant selectivity by upland field soil treatment)

In a plastic pot (surface area: 600 cm²) filled with upland field soil, wheat (Tr), barnyardgrass (Ec),green foxtail (Se), Johnsongrass (So), Alopecurus myosuroides (Al), pale smartweed (Po), slender amaranth (Am) and common lambsquarters (Ch) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 78 to 79.

                  TABLE 78                                                         ______________________________________                                                         Herbicidal           Phyto-                                    Compound                                                                               Dose    effect               toxicity                                  No.     (g.sup.ai /10a)                                                                        Ec     Se  So  Al   Po  Am   Ch  Tr                            ______________________________________                                          2      25      5      5   5   5    5   5    5   1                              4      25      5      5   5   5    5   5    5   1                              9      25      5      5   5   5    5   5    5   1                              10     25      5      5   5   5    5   5    5   1                              11     25      5      4   5   5    5   5    5   0                              12     25      5      5   5   5    5   5    5   1                              13     25      4      3   5   5    5   5    5   0                              24     25      5      4   5   5    5   5    5   0                              26     25      5      4   5   5    5   5    5   0                              40     25      4      5   5   3    5   5    5   0                              42     25      3      1   4   3    5   5    5   0                              61     25      5      5   5   5    5   5    3   0                              62     6.3     5      4   5   5    5   5    3   0                             507     25      5      5   5   5    5   5    5   0                             511     25      5      3   5   5    5   5    3   0                             512     6.3     5      3   5   5    5   5    5   0                             523     25      5      3   4   4    5   5    5   1                             525     6.3     5      3   5   5    5   5    5   0                             526     6.3     5      5   5   5    5   5    5   1                             527     6.3     5      5   5   5    5   5    5   0                             529     25      5      5   5   5    5   5    5   0                             531     25      5      5   5   5    5   5    5   0                             536     6.3     5      3   5   5    5   5    5   0                             ______________________________________                                    

                  TABLE 79                                                         ______________________________________                                                         Herbicidal           Phyto-                                    Compound                                                                               Dose    effect               toxicity                                  No.     (g.sup.ai /10a)                                                                        Ec     Se  So  Al   Po  Am   Ch  Tr                            ______________________________________                                         553     25      5      5   5   5    5   5    5   0                             554     25      5      5   5   5    5   5    5   0                             563     6.3     5      4   5   5    5   5    5   0                             591     6.3     3      4   5   5    5   5    5   0                             665     6.3     3      3   4   4    5   5    5   0                             787     6.3     3      5   5   5    5   5    5   3                             789     6.3     2      3   5   5    5   5    5   2                             Comparative                                                                            25      0      0   0   0    0   0    0   0                             compound A                                                                     Comparative                                                                            25      0      0   0   0    0   1    1   0                             compound B                                                                     Comparative                                                                            100     1      0   1   1    2   5    4   3                             compound C                                                                     Comparative                                                                            400     2      1   3   2    2   5    5   4                             compound D                                                                     Comparative                                                                            25      0      0   0   0    0   0    0   0                             compound E                                                                     Comparative                                                                            25      0      0   0   0    0   0    0   0                             compound F                                                                     ______________________________________                                    

TEST EXAMPLE 6 (Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm²) filled with upland field soil, rice (Or), wheat (Tr), barnyardgrass (Ec), Johnsongrass (So), Alopecurus myosucroides (Al), pale smartweed (Po), slender amaranth (Am) and common lambsquarters (Ch) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 80 and 81.

                  TABLE 80                                                         ______________________________________                                                          Herbicidal         Phyto-                                     Compound Dose    effect             toxicity                                   No.      (g.sup.ai /10a)                                                                        Ec    So   Al  Po  Am    Ch  Or  Tr                           ______________________________________                                          2       25      5     5    5   5   5     5   1   1                             4       25      5     5    5   5   5     5   0   0                             8       25      5     4    5   5   5     5   1   0                             9       25      5     5    5   5   5     5   0   0                             24      25      5     5    5   5   5     5   2   0                             26      25      5     5    5   5   5     5   1   0                             34      25      5     5    5   5   5     5   0   0                             35      25      5     5    5   5   5     5   0   0                             40      25      3     4    3   5   5     4   1   0                             42      25      3     3    3   4   4     4   1   0                             61      1.6     5     5    5   5   5     3   1   0                             62      25      5     5    5   5   5     5   0   0                            171      25      5     5    5   5   5     5   1   0                            262      25      5     5    4   4   5     3   0   0                            506      6.3     5     5    5   5   5     4   1   0                            507      6.3     5     5    5   5   5     3   1   0                            509      6.3     5     5    5   5   5     5   1   0                            511      25      5     5    5   5   5     5   2   0                            512      25      5     5    5   5   5     5   2   0                            522      25      5     5    5   5   5     5   2   0                            526      25      5     5    5   5   5     5   1   1                            527      6.3     5     5    5   5   5     5   1   0                            528      25      5     5    5   5   5     5   2   0                            529      6.3     5     5    5   5   5     5   1   0                            530      6.3     5     5    5   5   5     5   2   1                            531      1.6     5     5    5   5   5     5   1   0                            543      25      5     4    5   5   5     4   1   0                            547      6.3     5     5    5   5   5     4   2   0                            548      6.3     5     5    5   4   5     4   2   1                            549      6.3     5     5    5   5   5     5   0   0                            550      6.3     5     5    5   5   5     5   0   0                            551      6.3     5     5    5   5   5     5   2   0                            562      6.3     5     5    5   5   5     5   0   0                            ______________________________________                                    

                  TABLE 81                                                         ______________________________________                                                           Herbicidal         Phyto-                                    Compound                                                                               Dose      effect             toxicity                                  No.     (gai/10a) Ec    So  Al   Po  Am   Ch   Or  Tr                          ______________________________________                                         563     25        5     5   5    5   5    5    0   0                           567     25        5     5   5    5   5    4    1   0                           568     25        5     5   5    5   5    5    0   0                           578     6.3       5     5   5    5   5    4    1   1                           597     1.6       4     3   5    5   5    5    1   1                           848     25        2     3   5    5   5    5    1   0                           929     25        5     5   5    5   5    5    1   0                           Comparative                                                                            25        0     0   0    0   0    0    0   0                           compound A                                                                     Comparative                                                                            25        0     0   0    1   2    1    1   0                           compound B                                                                     Comparative                                                                            100       2     2   1    1   4    5    4   2                           compound C                                                                     Comparative                                                                            400       0     0   0    5   4    5    3   3                           compound D                                                                     Comparative                                                                            100       0     0   0    0   0    0    0   0                           compound E                                                                     Comparative                                                                            100       0     0   0    0   0    0    0   0                           compound F                                                                     ______________________________________                                     

We claim:
 1. A pyrimidine of the formula (I): ##STR514## wherein A is a heterocyclic ring of the formula: ##STR515## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ -alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br, a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ N(CH₂ CH₂ CH₂ CH₄)₄ !⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ;O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O--Na⁺ ; or a group of the formula --NR⁶ R⁷, wherein:each of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ -alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; each of R¹ and R², which may be the same or different, is a hydrogen atom; a formyl group; a C₁ -C₈ -alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ -cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ -alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³, wherein:R⁶ and R⁷ are as defined above; R⁸ is a hydrogen atom, a phenyl group, or a methyl group; R⁹ is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group; a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl; each of R¹⁰ and R¹¹, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a morpholine ring; and each of R¹² and R¹³, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R¹² and R¹³ may, together with the carbon atom to which they are bound, form a cyclopentylidene group; each of R³ and R⁴, which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C₁ -C₆ alkyl group; R⁵ is a hydrogen atom; a methyl group which may be substituted with methoxycarbonyl, ethoxycarbonyl, t-butylcarbonyloxy or methoxy; a formyl group; a C₁ -C₈ alkylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group; a carbomoyl group; a C₂ -C₄ alkoxycarbonyl group; a phenyloxycarbonyl group; a benzyloxycarbonyl group; a methylthiocarbonyl group; a phenylthiocarbonyl group; a methylsulfonyl group; a p-tolylsulfonyl group; a tri-C₁ -C₄ -alkylsilyl group; a propenyl group; a propynyl group; a 4,6-dimethoxypyridin-2-yl group or a trichloromethylthio group; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group or a cyanomethylene group, and Z is a nitrogen atom; or a salt thereof.
 2. A pyrimidine of the formula (I): ##STR516## wherein A is a heterocyclic ring of the formula: ##STR517## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ -alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br, a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O₋ N(CH₂ CH₂ CH₂ CH₄)₄ !⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O--Na⁺ ; or a group of the formula --NR⁶ R⁷, wherein:each of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ -alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; each of R¹ and R², which may be the same or different, is a hydrogen atom; a formyl group; a C₁ -C₈ -alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ -cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ -alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³, wherein:R⁶ and R⁷ are as defined above; R⁸ is a hydrogen atom, a phenyl group, or a methyl group; R⁹ is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group; a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl; each of R¹⁰ and R¹¹, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a morpholine ring; and each of R¹² and R¹³, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R¹² and R¹³ may, together with the carbon atom to which they are bound, form a cyclopentylidene group; provided that when A is of the formula (A-1), either R¹ or R² is a formyl group, a C₁ -C₈ -alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carbonyl group; a group of the formula --CONR⁶ R⁷ wherein R⁶ and R⁷ are as defined above; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ -cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ -alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; or a halogenated carbonyl group; each of R³ and R⁴, which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C₁ -C₆ alkyl group; R⁵ is a hydrogen atom; a methyl group which may be substituted with methoxycarbonyl, ethoxycarbonyl, t-butylcarbonyloxy or methoxy; a formyl group; a C₁ -C₈ alkylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group; a carbomoyl group; a C₂ -C₄ alkoxycarbonyl group; a phenyloxycarbonyl group; a benzyloxycarbonyl group; a methylthiocarbonyl group; a phenylthiocarbonyl group; a methylsulfonyl group; a p-tolylsulfonyl group; a tri-C₁ -C₄ -alkylsilyl group; a propenyl group; a propynyl group; a 4,6-dimethoxypyridin-2-yl group or a trichloromethylthio group; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group or a cyanomethylene group, and Z is a nitrogen atom; or a salt thereof.
 3. A triazine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-1), (A-2), (A-3) or (A-4), W is an oxygen atom or a sulfur atom, and each of R³ and R⁴ is an alkoxy group.
 4. An herbicidal composition containing an herbicidally effective amount of the triazine of claim 1 and a carrier therefor.
 5. An herbicidal composition containing an herbicidally effective amount of the triazine of claim 2 and a carrier therefor.
 6. An herbicidal composition containing an herbicidally effective amount of the triazine of claim 3 and a carrier therefor. 